-------------------------------------------------------------------------------
    References for the synthesis of gamma-butyrolactone from 1,4-butanediol
-------------------------------------------------------------------------------


Reactant BRN 1633445 butane-1,4-diol
Product BRN 105248 dihydro-furan-2-one
No. of Reaction Details 111
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Reaction Details 1 of 111

Reaction Classification Preparation
Temperature 200 C
Other Conditions Erhitzen mit einem Chrom(III)-oxid enth. Kupfer-Katalysator
Ref. 1 605477; Journal; Reppe et al.; JLACBF; Justus Liebigs Ann. Chem.; 596; 1955; 1, 158, 178;
-------------------------

Reaction Details 2 of 111

Reaction Classification Preparation
Other Conditions mit Hilfe von Acetobacter-Kulturen
Ref. 1 605476; Patent; Weinessigfabr. A. Enenkel; DE 929543; 1949;
-------------------------

Reaction Details 3 of 111

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent potassium dichromate
Solvent dimethylformamide
Time 20 hour(s)
Other Conditions Ambient temperature
Ref. 1 5611749; Journal; Kim, Kwan Soo; Szarek, Walter A.; CRBRAT; Carbohydr.Res.; EN; 104; 1982; 328-333;
-------------------------

Reaction Details 4 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent benzalacetone, Et3N
Catalyst Ru2Cl4((-)-DIOP)3
Time 5 hour(s)
Temperature 190 C
Ref. 1 5608240; Journal; Ishii, Youichi; Osakada, Kohtaro; Ikariya, Takao; Saburi, Masahiko; Yoshikawa, Sadao; CMLTAG;
Chem.Lett.; EN; 1982; 1179-1182;
-------------------------

Reaction Details 5 of 111

Reaction Classification Preparation
Yield 79 percent (BRN=105248)
Reagent allyl methyl carbonate
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3.5 hour(s)
Other Conditions Heating
Ref. 1 5611107; Journal; Minami, Ichiro; Tsuji, Jiro; TETRAB; Tetrahedron; EN; 43; 17; 1987; 3903-3916;
-------------------------

Reaction Details 6 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 35percent aq. hydrogen peroxide, tris(cetylpyridinium) 12-tungstophosphate (CWP)
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
Ref. 1 5639938; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Ura, Toshikazu; Yamada, Hiroshi; Yoshida, Tsutomu; Ogawa,
Masaya; JOCEAH; J.Org.Chem.; EN; 53; 15; 1988; 3587-3593;
-------------------------

Reaction Details 7 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent sodium bromite
Solvent H2O
acetic acid
Time 10 hour(s)
Other Conditions Ambient temperature
Ref. 1 5666548; Journal; Kageyama, Toshifumi; Kawahara, Shuji; Kitamura, Kohji; Ueno, Yoshio; Okawara, Makoto; CMLTAG;
Chem.Lett.; EN; 1983; 1097-1100;
-------------------------

Reaction Details 8 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 4-(benzoyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl, NaBr
Solvent CH2Cl2
H2O
Other Conditions NaHCO3-buffered at pH 8.6; electrolysis
Ref. 1 5584616; Journal; Inokuchi, Tsutomu; Matsumoto, Sigeaki; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 56; 7; 1991;
2416-2421;
-------------------------

Reaction Details 9 of 111

Reaction Classification Preparation
Yield 44 percent (BRN=105248)
Catalyst <(2,2'-bipyridine)(2,2':6',2''-terpyridine)RuO>2+ - complex
Time 20 hour(s)
Other Conditions Ambient temperature
buffer; electrooxidation: 56 mA current
Ref. 1 5532772; Journal; Navarro, Marcelo; Giovanni, Wagner F. De; Romero, Jose R.; TETRAB; Tetrahedron; EN; 47; 4/5; 1991;
851-857;
-------------------------

Reaction Details 10 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 11 of 111

Reaction Classification Preparation
Yield 74 percent Turnov (BRN=105248)
Reagent Phenyl bromide, K2CO3
Catalyst Pd(OAc)2, Triphenylphosphine
Solvent 1,2-dimethoxy-ethane
Time 12 hour(s)
Temperature 85 C
Ref. 1 5579141; Journal; Tamaru, Yoshinao; Yamada, Yoshimi; Inoue, Kenji; Yamamoto, Youichi; Yoshida, Zen-ichi; JOCEAH;
J.Org.Chem.; EN; 48; 8; 1983; 1286-1292;
-------------------------

Reaction Details 12 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (1,10-phenanthroline)H2CrOCl5
Solvent CH2Cl2
Time 8 hour(s)
Temperature 25 C
Ref. 1 5555229; Journal; Chakraborty, T. K.; Chandrasekaran, S.; TELEAY; Tetrahedron Lett.; EN; 21; 1980; 1583-1586;
-------------------------

Reaction Details 13 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent NaBrO2*3H2O, NaHCO3, 4-(benzyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl
Solvent CH2Cl2
H2O
Time 3 hour(s)
Other Conditions Ambient temperature
Ref. 1 5504352; Journal; Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 55;
2; 1990; 462-466;
-------------------------

Reaction Details 14 of 111

Reaction Classification Preparation
Yield 100 percent Chromat (BRN=105248)
Reagent acetone
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3 hour(s)
Temperature 180 C
Ref. 1 5554152; Journal; Murahashi, Shun-Ichi; Ito, Kei-ichiro; Naota, Takeshi; Maeda, Yoshihiro; TELEAY; Tetrahedron Lett.;
EN; 22; 52; 1981; 5327-5330;
-------------------------

Reaction Details 15 of 111

Reaction Classification Preparation
Yield 91.1 percent (BRN=105248)
Reagent O2
Catalyst Pd%0&, K-L zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 83.9 - 117.9 C
Pressure 757.6 Torr
Other Conditions other supporting zeolites, other solvents, other temperatures
Ref. 1 5506788; Journal; Baba, Toshihide; Kameta, Keiichiro; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; BCSJA8;
Bull.Chem.Soc.Jpn.; EN; 63; 1; 1990; 255-257;
-------------------------

Reaction Details 16 of 111

Reaction Classification Preparation
Yield 80 percent Chromat (BRN=105248)
Catalyst CuO
Time 15 hour(s)
Temperature 200 C
Note 1 Further byproducts given
Ref. 1 5549295; Journal; Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; TELEAY; Tetrahedron Lett.; FR; 22;
41; 1981; 4073-4076;
-------------------------

Reaction Details 17 of 111

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent AcOOH/NaBr
Solvent ethyl acetate
Time 2 hour(s)
Temperature 39.9 C
Ref. 1 5647691; Journal; Morimoto, Takashi; Hirano, Masao; Hamaguchi, Takayoshi; Shimoyama, Masahide; Zhuang, Xiumin;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 65; 3; 1992; 703-706;
-------------------------

Reaction Details 18 of 111

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Reagent RuH3(Ph3P)3
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 19 of 111

Reaction Classification Preparation
Yield 87 percent (BRN=105248)
Reagent trichloromelamine
Solvent CH2Cl2
Time 12 hour(s)
Other Conditions Ambient temperature
Ref. 1 5815102; Journal; Kondo, Shuji; Ohira, Mari; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; JOCEAH; J.Org.Chem.; EN;
58; 18; 1993; 5003-5004;
-------------------------

Reaction Details 20 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent oxygen
Catalyst Pd on Na-ZSM-5 zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 117.9 C
Ref. 1 5914130; Journal; Baba, T.; Kameta, K.; Nishiyama, S.; Tsuruya, S.; Masai, M.; JCCCAT; J.Chem.Soc.Chem.Commun.; EN;
15; 1989; 1072-1073;
-------------------------

Reaction Details 21 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent NaBrO2*3H20, Al2O3
Solvent CH2Cl2
Other Conditions Ambient temperature
Ref. 1 5895926; Journal; Morimoto, Takashi; Hirano, Masao; Iwasaki, Keiko; Ishikawa, Takashi; CMLTAG; Chem.Lett.; EN; 1;
1994; 53-54;
-------------------------

Reaction Details 22 of 111

Reaction Classification Preparation
Reagent 35percent H2O2
Catalyst tricetylpyridinium-12-tungstophosphate
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Temperature 82 C
Other Conditions Heating
Note 1 Yield given
Ref. 1 5740601; Journal; Yamawaki, K.; Nishihara, H.; Yoshida, T.; Ura, T.; Yamada, H.; et al.; SYNCAV; Synth.Commun.; EN;
18; 8; 1988; 869-876;
-------------------------

Reaction Details 23 of 111

Reaction Classification Preparation
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 24 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent 4-methoxy-1-oxo-2,2,6,6-tetranethylpiperidinium chloride
Solvent CH2Cl2
Time 10 min
Temperature 25 C
Ref. 1 5699448; Journal; Miyazawa, Takeo; Endo, Takeshi; JOCEAH; J.Org.Chem.; EN; 50; 20; 1985; 3930-3931;
-------------------------

Reaction Details 25 of 111

Reaction Classification Preparation
Yield 60 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent CCl4
H2O
Time 5.5 hour(s)
Temperature 70 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
-------------------------

Reaction Details 26 of 111

Reaction Classification Preparation
Yield 58 percent (BRN=105248)
Reagent KMnO4, CuSO4*5H2O
Solvent CH2Cl2
Ref. 1 5932996; Journal; Jefford, Charles W.; Wang, Ying; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 10; 1988; 634-635;
-------------------------

Reaction Details 27 of 111

Reaction Classification Preparation
Yield 78 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CCl4
Time 5 hour(s)
Temperature 37 C
Ref. 1 5934286; Journal; Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 59; 3; 1986; 747-750;
-------------------------

Reaction Details 28 of 111

Reaction Classification Preparation
Yield 66 percent Chromat (BRN=105248)
Reagent tris(cetylpyridinium) peroxo-12-molybdophosphate (PCMP)
Solvent benzene
Time 2 hour(s)
Other Conditions Heating
Ref. 1 5952228; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Yoshida, Tsutomu; Ura, Toshikazu; Ogawa, Masaya; JOCEAH;
J.Org.Chem.; EN; 52; 9; 1987; 1868-1870;
-------------------------

Reaction Details 29 of 111

Reaction Classification Preparation
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 30 of 111

Reaction Classification Preparation
Yield 62 percent (BRN=105248)
Reagent aq. NaBrO3, aq. NaHSO3
Solvent acetonitrile
Time 2 hour(s)
Other Conditions Heating
Ref. 1 6008056; Journal; Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii,
Yasutaka; CMLTAG; Chem.Lett.; EN; 10; 1995; 871-872;
-------------------------

Reaction Details 31 of 111

Reaction Classification Preparation
Yield 50 percent (BRN=105248)
Reagent tert-butyl hydroperoxide, 3A molecular sieves
Catalyst Zr(O-n-Pr)4
Solvent CH2Cl2
Time 2 day(s)
Temperature 60 C
Ref. 1 6012392; Journal; Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; JOCEAH; J.Org.Chem.; EN; 61; 4; 1996; 1467-1472;
-------------------------

Reaction Details 32 of 111

Reaction Classification Chemical behaviour
Reagent tris(cetylpyridinium) 12-tungstophosphate (CWP), 35percent H2O2
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
other $a,$w-diols; var. solvents and reagents
Subject Studied Product distribution
Ref. 1 5639734; Journal; Ishii, Yasutaka; Yoshida, Tsutomu; Yamawaki, Kazumasa; Ogawa, Masaya; JOCEAH; J.Org.Chem.; EN;
53; 23; 1988; 5549-5552;
-------------------------

Reaction Details 33 of 111

Reaction Classification Chemical behaviour
Yield 85 percent (BRN=105248)
Reagent RuH4(iPr3P)2
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Other Conditions other diols, var. transition metal polyhydrides and reaction conditions
Subject Studied Mechanism
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 34 of 111

Reaction Classification Chemical behaviour
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
other oxidant, other substrate
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 35 of 111

Reaction Classification Chemical behaviour
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
var. time of reaction' var. diols
Subject Studied Mechanism
Product distribution
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 36 of 111

Reaction Classification Chemical behaviour
Reagent cyclohexanone
Catalyst RuHClCO(PPh3)3
Time 20 hour(s)
Temperature 140 C
Other Conditions hydrogen transfer; further carbonyl compounds, further ruthenium(II) catalysts
Ref. 1 5769676; Journal; Marcec, Radovan; ZNBAD2; Z.Naturforsch.B Anorg.Chem.Org.Chem.; EN; 39; 12; 1984; 1823-1824;
-------------------------

Reaction Details 37 of 111

Reaction Classification Chemical behaviour
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Other Conditions var. solvents, other $a,$w-diol
Subject Studied Product distribution
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 38 of 111

Reaction Classification Preparation
Temperature 200 C
Other Conditions Erhitzen mit einem Chrom(III)-oxid enth. Kupfer-Katalysator
Ref. 1 605477; Journal; Reppe et al.; JLACBF; Justus Liebigs Ann. Chem.; 596; 1955; 1, 158, 178;
-------------------------

Reaction Details 39 of 111

Reaction Classification Preparation
Other Conditions mit Hilfe von Acetobacter-Kulturen
Ref. 1 605476; Patent; Weinessigfabr. A. Enenkel; DE 929543; 1949;
-------------------------

Reaction Details 40 of 111

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent potassium dichromate
Solvent dimethylformamide
Time 20 hour(s)
Other Conditions Ambient temperature
Ref. 1 5611749; Journal; Kim, Kwan Soo; Szarek, Walter A.; CRBRAT; Carbohydr.Res.; EN; 104; 1982; 328-333;

Ref. 1 5611749; Journal; Kim, Kwan Soo; Szarek, Walter A.; CRBRAT; Carbohydr.Res.; EN; 104; 1982; 328-333;
-------------------------

Reaction Details 41 of 111

Reaction Classification Chemical behaviour
Reagent tris(cetylpyridinium) 12-tungstophosphate (CWP), 35percent H2O2
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
other $a,$w-diols; var. solvents and reagents
Subject Studied Product distribution
Ref. 1 5639734; Journal; Ishii, Yasutaka; Yoshida, Tsutomu; Yamawaki, Kazumasa; Ogawa, Masaya; JOCEAH; J.Org.Chem.; EN;
53; 23; 1988; 5549-5552;
-------------------------

Reaction Details 42 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent benzalacetone, Et3N
Catalyst Ru2Cl4((-)-DIOP)3
Time 5 hour(s)
Temperature 190 C
Ref. 1 5608240; Journal; Ishii, Youichi; Osakada, Kohtaro; Ikariya, Takao; Saburi, Masahiko; Yoshikawa, Sadao; CMLTAG;
Chem.Lett.; EN; 1982; 1179-1182;
-------------------------

Reaction Details 43 of 111

Reaction Classification Chemical behaviour
Yield 85 percent (BRN=105248)
Reagent RuH4(iPr3P)2
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Other Conditions other diols, var. transition metal polyhydrides and reaction conditions
Subject Studied Mechanism
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 44 of 111

Reaction Classification Preparation
Yield 79 percent (BRN=105248)
Reagent allyl methyl carbonate
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3.5 hour(s)
Other Conditions Heating
Ref. 1 5611107; Journal; Minami, Ichiro; Tsuji, Jiro; TETRAB; Tetrahedron; EN; 43; 17; 1987; 3903-3916;
-------------------------

Reaction Details 45 of 111

Reaction Classification Chemical behaviour
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
other oxidant, other substrate
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 46 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 35percent aq. hydrogen peroxide, tris(cetylpyridinium) 12-tungstophosphate (CWP)
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
Ref. 1 5639938; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Ura, Toshikazu; Yamada, Hiroshi; Yoshida, Tsutomu; Ogawa,
Masaya; JOCEAH; J.Org.Chem.; EN; 53; 15; 1988; 3587-3593;
-------------------------

Reaction Details 47 of 111

Reaction Classification Chemical behaviour
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
var. time of reaction' var. diols
Subject Studied Mechanism
Product distribution
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 48 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent sodium bromite
Solvent H2O
acetic acid
Time 10 hour(s)
Other Conditions Ambient temperature
Ref. 1 5666548; Journal; Kageyama, Toshifumi; Kawahara, Shuji; Kitamura, Kohji; Ueno, Yoshio; Okawara, Makoto; CMLTAG;
Chem.Lett.; EN; 1983; 1097-1100;
-------------------------

Reaction Details 49 of 111

Reaction Classification Chemical behaviour
Reagent cyclohexanone
Catalyst RuHClCO(PPh3)3
Time 20 hour(s)
Temperature 140 C
Other Conditions hydrogen transfer; further carbonyl compounds, further ruthenium(II) catalysts
Ref. 1 5769676; Journal; Marcec, Radovan; ZNBAD2; Z.Naturforsch.B Anorg.Chem.Org.Chem.; EN; 39; 12; 1984; 1823-1824;
-------------------------

Reaction Details 50 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 4-(benzoyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl, NaBr
Solvent CH2Cl2
H2O
Other Conditions NaHCO3-buffered at pH 8.6; electrolysis
Ref. 1 5584616; Journal; Inokuchi, Tsutomu; Matsumoto, Sigeaki; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 56; 7; 1991;
2416-2421;
-------------------------

Reaction Details 51 of 111

Reaction Classification Preparation
Yield 44 percent (BRN=105248)
Catalyst <(2,2'-bipyridine)(2,2':6',2''-terpyridine)RuO>2+ - complex
Time 20 hour(s)
Other Conditions Ambient temperature
buffer; electrooxidation: 56 mA current
Ref. 1 5532772; Journal; Navarro, Marcelo; Giovanni, Wagner F. De; Romero, Jose R.; TETRAB; Tetrahedron; EN; 47; 4/5; 1991;
851-857;
-------------------------

Reaction Details 52 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 53 of 111

Reaction Classification Preparation
Yield 74 percent Turnov (BRN=105248)
Reagent Phenyl bromide, K2CO3
Catalyst Pd(OAc)2, Triphenylphosphine
Solvent 1,2-dimethoxy-ethane
Time 12 hour(s)
Temperature 85 C
Ref. 1 5579141; Journal; Tamaru, Yoshinao; Yamada, Yoshimi; Inoue, Kenji; Yamamoto, Youichi; Yoshida, Zen-ichi; JOCEAH;
J.Org.Chem.; EN; 48; 8; 1983; 1286-1292;
-------------------------

Reaction Details 54 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (1,10-phenanthroline)H2CrOCl5
Solvent CH2Cl2
Time 8 hour(s)
Temperature 25 C
Ref. 1 5555229; Journal; Chakraborty, T. K.; Chandrasekaran, S.; TELEAY; Tetrahedron Lett.; EN; 21; 1980; 1583-1586;
-------------------------

Reaction Details 55 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent NaBrO2*3H2O, NaHCO3, 4-(benzyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl
Solvent CH2Cl2
H2O
Time 3 hour(s)
Other Conditions Ambient temperature
Ref. 1 5504352; Journal; Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 55;
2; 1990; 462-466;
-------------------------

Reaction Details 56 of 111

Reaction Classification Preparation
Yield 100 percent Chromat (BRN=105248)
Reagent acetone
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3 hour(s)
Temperature 180 C
Ref. 1 5554152; Journal; Murahashi, Shun-Ichi; Ito, Kei-ichiro; Naota, Takeshi; Maeda, Yoshihiro; TELEAY; Tetrahedron Lett.;
EN; 22; 52; 1981; 5327-5330;
-------------------------

Reaction Details 57 of 111

Reaction Classification Preparation
Yield 91.1 percent (BRN=105248)
Reagent O2
Catalyst Pd%0&, K-L zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 83.9 - 117.9 C
Pressure 757.6 Torr
Other Conditions other supporting zeolites, other solvents, other temperatures
Ref. 1 5506788; Journal; Baba, Toshihide; Kameta, Keiichiro; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; BCSJA8;
Bull.Chem.Soc.Jpn.; EN; 63; 1; 1990; 255-257;
-------------------------

Reaction Details 58 of 111

Reaction Classification Preparation
Yield 80 percent Chromat (BRN=105248)
Catalyst CuO
Time 15 hour(s)
Temperature 200 C
Note 1 Further byproducts given
Ref. 1 5549295; Journal; Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; TELEAY; Tetrahedron Lett.; FR; 22;
41; 1981; 4073-4076;
-------------------------

Reaction Details 59 of 111

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent AcOOH/NaBr
Solvent ethyl acetate
Time 2 hour(s)
Temperature 39.9 C
Ref. 1 5647691; Journal; Morimoto, Takashi; Hirano, Masao; Hamaguchi, Takayoshi; Shimoyama, Masahide; Zhuang, Xiumin;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 65; 3; 1992; 703-706;
-------------------------

Reaction Details 60 of 111

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Reagent RuH3(Ph3P)3
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 61 of 111

Reaction Classification Preparation
Yield 87 percent (BRN=105248)
Reagent trichloromelamine
Solvent CH2Cl2
Time 12 hour(s)
Other Conditions Ambient temperature
Ref. 1 5815102; Journal; Kondo, Shuji; Ohira, Mari; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; JOCEAH; J.Org.Chem.; EN;
58; 18; 1993; 5003-5004;
-------------------------

Reaction Details 62 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent oxygen
Catalyst Pd on Na-ZSM-5 zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 117.9 C
Ref. 1 5914130; Journal; Baba, T.; Kameta, K.; Nishiyama, S.; Tsuruya, S.; Masai, M.; JCCCAT; J.Chem.Soc.Chem.Commun.; EN;
15; 1989; 1072-1073;
-------------------------

Reaction Details 63 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent NaBrO2*3H20, Al2O3
Solvent CH2Cl2
Other Conditions Ambient temperature
Ref. 1 5895926; Journal; Morimoto, Takashi; Hirano, Masao; Iwasaki, Keiko; Ishikawa, Takashi; CMLTAG; Chem.Lett.; EN; 1;
1994; 53-54;
-------------------------

Reaction Details 64 of 111

Reaction Classification Preparation
Reagent 35percent H2O2
Catalyst tricetylpyridinium-12-tungstophosphate
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Temperature 82 C
Other Conditions Heating
Note 1 Yield given
Ref. 1 5740601; Journal; Yamawaki, K.; Nishihara, H.; Yoshida, T.; Ura, T.; Yamada, H.; et al.; SYNCAV; Synth.Commun.; EN;
18; 8; 1988; 869-876;
-------------------------

Reaction Details 65 of 111

Reaction Classification Preparation
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 66 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent 4-methoxy-1-oxo-2,2,6,6-tetranethylpiperidinium chloride
Solvent CH2Cl2
Time 10 min
Temperature 25 C
Ref. 1 5699448; Journal; Miyazawa, Takeo; Endo, Takeshi; JOCEAH; J.Org.Chem.; EN; 50; 20; 1985; 3930-3931;
-------------------------

Reaction Details 67 of 111

Reaction Classification Preparation
Yield 60 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent CCl4
H2O
Time 5.5 hour(s)
Temperature 70 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
-------------------------

Reaction Details 68 of 111

Reaction Classification Preparation
Yield 58 percent (BRN=105248)
Reagent KMnO4, CuSO4*5H2O
Solvent CH2Cl2
Ref. 1 5932996; Journal; Jefford, Charles W.; Wang, Ying; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 10; 1988; 634-635;
-------------------------

Reaction Details 69 of 111

Reaction Classification Preparation
Yield 78 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CCl4
Time 5 hour(s)
Temperature 37 C
Ref. 1 5934286; Journal; Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 59; 3; 1986; 747-750;
-------------------------

Reaction Details 70 of 111

Reaction Classification Preparation
Yield 66 percent Chromat (BRN=105248)
Reagent tris(cetylpyridinium) peroxo-12-molybdophosphate (PCMP)
Solvent benzene
Time 2 hour(s)
Other Conditions Heating
Ref. 1 5952228; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Yoshida, Tsutomu; Ura, Toshikazu; Ogawa, Masaya; JOCEAH;
J.Org.Chem.; EN; 52; 9; 1987; 1868-1870;
-------------------------

Reaction Details 71 of 111

Reaction Classification Chemical behaviour
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Other Conditions var. solvents, other $a,$w-diol
Subject Studied Product distribution
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 72 of 111

Reaction Classification Preparation
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 73 of 111

Reaction Classification Preparation
Yield 62 percent (BRN=105248)
Reagent aq. NaBrO3, aq. NaHSO3
Solvent acetonitrile
Time 2 hour(s)
Other Conditions Heating
Ref. 1 6008056; Journal; Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii,
Yasutaka; CMLTAG; Chem.Lett.; EN; 10; 1995; 871-872;
-------------------------

Reaction Details 74 of 111

Reaction Classification Preparation
Yield 50 percent (BRN=105248)
Reagent tert-butyl hydroperoxide, 3A molecular sieves
Catalyst Zr(O-n-Pr)4
Solvent CH2Cl2
Time 2 day(s)
Temperature 60 C
Ref. 1 6012392; Journal; Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; JOCEAH; J.Org.Chem.; EN; 61; 4; 1996; 1467-1472;
-------------------------

Reaction Details 75 of 111

Reaction Classification Preparation
Temperature 200 C
Other Conditions Erhitzen mit einem Chrom(III)-oxid enth. Kupfer-Katalysator
Ref. 1 605477; Journal; Reppe et al.; JLACBF; Justus Liebigs Ann. Chem.; 596; 1955; 1, 158, 178;
-------------------------

Reaction Details 76 of 111

Reaction Classification Preparation
Other Conditions mit Hilfe von Acetobacter-Kulturen
Ref. 1 605476; Patent; Weinessigfabr. A. Enenkel; DE 929543; 1949;
-------------------------

Reaction Details 77 of 111

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent potassium dichromate
Solvent dimethylformamide
Time 20 hour(s)
Other Conditions Ambient temperature
Ref. 1 5611749; Journal; Kim, Kwan Soo; Szarek, Walter A.; CRBRAT; Carbohydr.Res.; EN; 104; 1982; 328-333;
-------------------------

------------------
-the good reverend drone

Ipsa scientia potestas est


   posted 01-20-2000 10:40 AM

Reaction Details 78 of 111

Reaction Classification Chemical behaviour
Reagent tris(cetylpyridinium) 12-tungstophosphate (CWP), 35percent H2O2
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
other $a,$w-diols; var. solvents and reagents
Subject Studied Product distribution
Ref. 1 5639734; Journal; Ishii, Yasutaka; Yoshida, Tsutomu; Yamawaki, Kazumasa; Ogawa, Masaya; JOCEAH; J.Org.Chem.; EN;
53; 23; 1988; 5549-5552;
-------------------------

Reaction Details 79 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent benzalacetone, Et3N
Catalyst Ru2Cl4((-)-DIOP)3
Time 5 hour(s)
Temperature 190 C
Ref. 1 5608240; Journal; Ishii, Youichi; Osakada, Kohtaro; Ikariya, Takao; Saburi, Masahiko; Yoshikawa, Sadao; CMLTAG;
Chem.Lett.; EN; 1982; 1179-1182;
-------------------------

Reaction Details 80 of 111

Reaction Classification Chemical behaviour
Yield 85 percent (BRN=105248)
Reagent RuH4(iPr3P)2
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Other Conditions other diols, var. transition metal polyhydrides and reaction conditions
Subject Studied Mechanism
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 81 of 111

Reaction Classification Preparation
Yield 79 percent (BRN=105248)
Reagent allyl methyl carbonate
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3.5 hour(s)
Other Conditions Heating
Ref. 1 5611107; Journal; Minami, Ichiro; Tsuji, Jiro; TETRAB; Tetrahedron; EN; 43; 17; 1987; 3903-3916;
-------------------------

Reaction Details 82 of 111

Reaction Classification Chemical behaviour
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
other oxidant, other substrate
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 83 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 35percent aq. hydrogen peroxide, tris(cetylpyridinium) 12-tungstophosphate (CWP)
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Other Conditions Heating
Ref. 1 5639938; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Ura, Toshikazu; Yamada, Hiroshi; Yoshida, Tsutomu; Ogawa,
Masaya; JOCEAH; J.Org.Chem.; EN; 53; 15; 1988; 3587-3593;
-------------------------

Reaction Details 84 of 111

Reaction Classification Chemical behaviour
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
var. time of reaction' var. diols
Subject Studied Mechanism
Product distribution
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 85 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent sodium bromite
Solvent H2O
acetic acid
Time 10 hour(s)
Other Conditions Ambient temperature
Ref. 1 5666548; Journal; Kageyama, Toshifumi; Kawahara, Shuji; Kitamura, Kohji; Ueno, Yoshio; Okawara, Makoto; CMLTAG;
Chem.Lett.; EN; 1983; 1097-1100;
-------------------------

Reaction Details 86 of 111

Reaction Classification Chemical behaviour
Reagent cyclohexanone
Catalyst RuHClCO(PPh3)3
Time 20 hour(s)
Temperature 140 C
Other Conditions hydrogen transfer; further carbonyl compounds, further ruthenium(II) catalysts
Ref. 1 5769676; Journal; Marcec, Radovan; ZNBAD2; Z.Naturforsch.B Anorg.Chem.Org.Chem.; EN; 39; 12; 1984; 1823-1824;
-------------------------

Reaction Details 87 of 111

Reaction Classification Preparation
Yield 97 percent (BRN=105248)
Reagent 4-(benzoyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl, NaBr
Solvent CH2Cl2
H2O
Other Conditions NaHCO3-buffered at pH 8.6; electrolysis
Ref. 1 5584616; Journal; Inokuchi, Tsutomu; Matsumoto, Sigeaki; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 56; 7; 1991;
2416-2421;
-------------------------

Reaction Details 88 of 111

Reaction Classification Preparation
Yield 44 percent (BRN=105248)
Catalyst <(2,2'-bipyridine)(2,2':6',2''-terpyridine)RuO>2+ - complex
Time 20 hour(s)
Other Conditions Ambient temperature
buffer; electrooxidation: 56 mA current
Ref. 1 5532772; Journal; Navarro, Marcelo; Giovanni, Wagner F. De; Romero, Jose R.; TETRAB; Tetrahedron; EN; 47; 4/5; 1991;
851-857;
-------------------------

Reaction Details 89 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (bipy)H2CrOCl5
Solvent CH2Cl2
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5574719; Journal; Chakraborty, T. K.; Bhushan, Vidya; Chandrasekaran, S.; IJSBDB; Indian J.Chem.Sect.B; EN; 22; 1;
1983; 9-11;
-------------------------

Reaction Details 90 of 111

Reaction Classification Preparation
Yield 74 percent Turnov (BRN=105248)
Reagent Phenyl bromide, K2CO3
Catalyst Pd(OAc)2, Triphenylphosphine
Solvent 1,2-dimethoxy-ethane
Time 12 hour(s)
Temperature 85 C
Ref. 1 5579141; Journal; Tamaru, Yoshinao; Yamada, Yoshimi; Inoue, Kenji; Yamamoto, Youichi; Yoshida, Zen-ichi; JOCEAH;
J.Org.Chem.; EN; 48; 8; 1983; 1286-1292;
-------------------------

Reaction Details 91 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent (1,10-phenanthroline)H2CrOCl5
Solvent CH2Cl2
Time 8 hour(s)
Temperature 25 C
Ref. 1 5555229; Journal; Chakraborty, T. K.; Chandrasekaran, S.; TELEAY; Tetrahedron Lett.; EN; 21; 1980; 1583-1586;
-------------------------

Reaction Details 92 of 111

Reaction Classification Preparation
Yield 95 percent (BRN=105248)
Reagent NaBrO2*3H2O, NaHCO3, 4-(benzyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl
Solvent CH2Cl2
H2O
Time 3 hour(s)
Other Conditions Ambient temperature
Ref. 1 5504352; Journal; Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru; JOCEAH; J.Org.Chem.; EN; 55;
2; 1990; 462-466;
-------------------------

Reaction Details 93 of 111

Reaction Classification Preparation
Yield 100 percent Chromat (BRN=105248)
Reagent acetone
Catalyst RuH2(PPh3)4
Solvent toluene
Time 3 hour(s)
Temperature 180 C
Ref. 1 5554152; Journal; Murahashi, Shun-Ichi; Ito, Kei-ichiro; Naota, Takeshi; Maeda, Yoshihiro; TELEAY; Tetrahedron Lett.;
EN; 22; 52; 1981; 5327-5330;
-------------------------

Reaction Details 94 of 111

Reaction Classification Preparation
Yield 91.1 percent (BRN=105248)
Reagent O2
Catalyst Pd%0&, K-L zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 83.9 - 117.9 C
Pressure 757.6 Torr
Other Conditions other supporting zeolites, other solvents, other temperatures
Ref. 1 5506788; Journal; Baba, Toshihide; Kameta, Keiichiro; Nishiyama, Satoru; Tsuruya, Shigeru; Masai, Mitsuo; BCSJA8;
Bull.Chem.Soc.Jpn.; EN; 63; 1; 1990; 255-257;
-------------------------

Reaction Details 95 of 111

Reaction Classification Preparation
Yield 80 percent Chromat (BRN=105248)
Catalyst CuO
Time 15 hour(s)
Temperature 200 C
Note 1 Further byproducts given
Ref. 1 5549295; Journal; Berthon, Bruno; Forestiere, Alain; Leleu, Gerard; Sillion, Bernard; TELEAY; Tetrahedron Lett.; FR; 22;
41; 1981; 4073-4076;
-------------------------

Reaction Details 96 of 111

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent AcOOH/NaBr
Solvent ethyl acetate
Time 2 hour(s)
Temperature 39.9 C
Ref. 1 5647691; Journal; Morimoto, Takashi; Hirano, Masao; Hamaguchi, Takayoshi; Shimoyama, Masahide; Zhuang, Xiumin;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 65; 3; 1992; 703-706;
-------------------------

Reaction Details 97 of 111

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Reagent RuH3(Ph3P)3
Solvent benzene
Time 24 hour(s)
Temperature 40 C
Ref. 1 5645533; Journal; Lin, Yingrui; Zhu, Xianchao; Zhou, Yuefen; JORCAI; J.Organomet.Chem.; EN; 429; 2; 1992; 269-274;
-------------------------

Reaction Details 98 of 111

Reaction Classification Preparation
Yield 87 percent (BRN=105248)
Reagent trichloromelamine
Solvent CH2Cl2
Time 12 hour(s)
Other Conditions Ambient temperature
Ref. 1 5815102; Journal; Kondo, Shuji; Ohira, Mari; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; JOCEAH; J.Org.Chem.; EN;
58; 18; 1993; 5003-5004;
-------------------------

Reaction Details 99 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent oxygen
Catalyst Pd on Na-ZSM-5 zeolite
Solvent various solvent(s)
Time 24 hour(s)
Temperature 117.9 C
Ref. 1 5914130; Journal; Baba, T.; Kameta, K.; Nishiyama, S.; Tsuruya, S.; Masai, M.; JCCCAT; J.Chem.Soc.Chem.Commun.; EN;
15; 1989; 1072-1073;
-------------------------

Reaction Details 100 of 111

Reaction Classification Preparation
Yield 92 percent (BRN=105248)
Reagent NaBrO2*3H20, Al2O3
Solvent CH2Cl2
Other Conditions Ambient temperature
Ref. 1 5895926; Journal; Morimoto, Takashi; Hirano, Masao; Iwasaki, Keiko; Ishikawa, Takashi; CMLTAG; Chem.Lett.; EN; 1;
1994; 53-54;
-------------------------

Reaction Details 101 of 111

Reaction Classification Preparation
Reagent 35percent H2O2
Catalyst tricetylpyridinium-12-tungstophosphate
Solvent 2-methyl-propan-2-ol
Time 24 hour(s)
Temperature 82 C
Other Conditions Heating
Note 1 Yield given
Ref. 1 5740601; Journal; Yamawaki, K.; Nishihara, H.; Yoshida, T.; Ura, T.; Yamada, H.; et al.; SYNCAV; Synth.Commun.; EN;
18; 8; 1988; 869-876;
-------------------------

Reaction Details 102 of 111

Reaction Classification Preparation
Yield 89 percent (BRN=105248)
Reagent N-iodosuccinimide, silver acetate
Solvent benzene
Time 7.5 hour(s)
Other Conditions Heating
Ref. 1 5747330; Journal; Beebe, Thomas R.; Adkins, Rick; Baldridge, Ruth; Hensley, Vivian; McMillen, Doug; et al.; JOCEAH;
J.Org.Chem.; EN; 52; 24; 1987; 5472-5474;
-------------------------

Reaction Details 103 of 111

Reaction Classification Preparation
Yield 81 percent (BRN=105248)
Reagent 4-methoxy-1-oxo-2,2,6,6-tetranethylpiperidinium chloride
Solvent CH2Cl2
Time 10 min
Temperature 25 C
Ref. 1 5699448; Journal; Miyazawa, Takeo; Endo, Takeshi; JOCEAH; J.Org.Chem.; EN; 50; 20; 1985; 3930-3931;
-------------------------

Reaction Details 104 of 111

Reaction Classification Preparation
Yield 60 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent CCl4
H2O
Time 5.5 hour(s)
Temperature 70 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
-------------------------

Reaction Details 105 of 111

Reaction Classification Preparation
Yield 58 percent (BRN=105248)
Reagent KMnO4, CuSO4*5H2O
Solvent CH2Cl2
Ref. 1 5932996; Journal; Jefford, Charles W.; Wang, Ying; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 10; 1988; 634-635;
-------------------------

Reaction Details 106 of 111

Reaction Classification Preparation
Yield 78 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CCl4
Time 5 hour(s)
Temperature 37 C
Ref. 1 5934286; Journal; Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo;
BCSJA8; Bull.Chem.Soc.Jpn.; EN; 59; 3; 1986; 747-750;
-------------------------

Reaction Details 107 of 111

Reaction Classification Preparation
Yield 66 percent Chromat (BRN=105248)
Reagent tris(cetylpyridinium) peroxo-12-molybdophosphate (PCMP)
Solvent benzene
Time 2 hour(s)
Other Conditions Heating
Ref. 1 5952228; Journal; Ishii, Yasutaka; Yamawaki, Kazumasa; Yoshida, Tsutomu; Ura, Toshikazu; Ogawa, Masaya; JOCEAH;
J.Org.Chem.; EN; 52; 9; 1987; 1868-1870;
-------------------------

Reaction Details 108 of 111

Reaction Classification Chemical behaviour
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Other Conditions var. solvents, other $a,$w-diol
Subject Studied Product distribution
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 109 of 111

Reaction Classification Preparation
Yield 88 percent (BRN=105248)
Reagent N-chlorosuccinimide
Solvent CH2Cl2
Time 5 hour(s)
Temperature 20 C
Ref. 1 5957676; Journal; Kondo, Shuji; Kawasoe, Shinya; Kunisada, Hideo; Yuki, Yasuo; SYNCAV; Synth.Commun.; EN; 25; 5;
1995; 719-724;
-------------------------

Reaction Details 110 of 111

Reaction Classification Preparation
Yield 62 percent (BRN=105248)
Reagent aq. NaBrO3, aq. NaHSO3
Solvent acetonitrile
Time 2 hour(s)
Other Conditions Heating
Ref. 1 6008056; Journal; Takase, Kiyoshi; Masuda, Haruyoshi; Kai, Osamu; Nishiyama, Yutaka; Sakaguchi, Satoshi; Ishii,
Yasutaka; CMLTAG; Chem.Lett.; EN; 10; 1995; 871-872;
-------------------------

Reaction Details 111 of 111

Reaction Classification Preparation
Yield 50 percent (BRN=105248)
Reagent tert-butyl hydroperoxide, 3A molecular sieves
Catalyst Zr(O-n-Pr)4
Solvent CH2Cl2
Time 2 day(s)
Temperature 60 C
Ref. 1 6012392; Journal; Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; JOCEAH; J.Org.Chem.; EN; 61; 4; 1996; 1467-1472;

------------------
-the good reverend drone

Ipsa scientia potestas est
