-------------------------------------------------------------------------------
References for the synthesis of gamma-butyrolactone from tetrahydrofuran (THF)
-------------------------------------------------------------------------------

Just to make this a more thorough study, here are a few more ref's for a few
more procedures worth looking at. I think you'll like them; the oxidation of THF
into butyrloactone is a calssic, and is the basis of a huge number of studies.
Enjoy. Gratis a Beilstein magnificum

Reaction

Reaction ID 3614
Reactant BRN 102391 tetrahydrofuran
Product BRN 105248 dihydro-furan-2-one
No. of Reaction Details 77
-------------------------

Reaction Details 1 of 77

Reaction Classification Preparation
Reagent water
hydrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 2 of 77

Reaction Classification Preparation
Reagent aqueous HNO3
benzene
Temperature 25 C
Ref. 1 605467; Journal; Moschkin; Trudy Sovesc. Vopr. Ispolz. Pentozan. Syria Riga; 1955; 225, 244; Chem.Abstr.; 1959; 15048;
-------------------------

Reaction Details 3 of 77

Reaction Classification Preparation
Reagent water
nitrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 4 of 77

Reaction Classification Preparation
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
-------------------------

Reaction Details 5 of 77

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent ZnCr2O7*3H2O
Solvent CH2Cl2
Time 1.0 hour(s)
Other Conditions Ambient temperature
Ref. 1 5572812; Journal; Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.; SYNTBF; Synthesis; EN; 4; 1986;
285-288;
-------------------------

Reaction Details 6 of 77

Reaction Classification Preparation
Yield 98 percent (BRN=105248)
Reagent trans-<Ru%VI&(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)O2><ClO4>2
Solvent acetonitrile
Time 1 hour(s)
Temperature 25 C
Ref. 1 5541107; Journal; Che, Chi-Ming; Tang, Wai-Tong; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 12; 1990;
3735-3739;
-------------------------

Reaction Details 7 of 77

Reaction Classification Preparation
Yield 80 percent (BRN=105248)
Reagent <Ru%V&L(O)>%2+&-complex <HL = <2-hydroxy-2-(2-pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent acetonitrile
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
-------------------------

Reaction Details 8 of 77

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Catalyst trans-<Ru(VI)(dmpipy)2O2><ClO4>2
Solvent acetonitrile
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5538120; Journal; Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 3; 1991; 379-384;
-------------------------

Reaction Details 9 of 77

Reaction Classification Preparation
Yield 68 percent (BRN=105248)
Reagent Ca(OCl)2
Solvent acetic acid
acetonitrile
H2O
Time 1 hour(s)
Temperature 0 C
Ref. 1 5554344; Journal; Nwaukwa, Stephen O.; Keehn, Philip M.; TELEAY; Tetrahedron Lett.; EN; 23; 1982; 35-38;
-------------------------

Reaction Details 10 of 77

Reaction Classification Preparation
Yield 60 percent Chromat (BRN=105248)
Reagent O2, tris(acetylacetonato)Co(III), 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
-------------------------

Reaction Details 11 of 77

Reaction Classification Preparation
Yield 41 percent (BRN=105248)
Reagent cis-<Ru%VI&(6,6'-Cl2bpy)2O2><ClO4>
Solvent acetonitrile
Time 90 min
Temperature 25 C
Ref. 1 5911524; Journal; Che, Chi-Ming; Leung, Wai-Ho; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 18; 1987; 1376-1377;
-------------------------

Reaction Details 12 of 77

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent Mn2O7
Solvent CCl4
acetone
Temperature -45 C
Ref. 1 5689808; Journal; Troemel, Martin; Russ, Manuel; ANCEAD; Angew.Chem.; GE; 99; 10; 1987; 1037-1038;
-------------------------

Reaction Details 13 of 77

Reaction Classification Preparation
Yield 11 percent (BRN=105248)
Reagent N-hydroxyphthalimide
Solvent pyridine
Other Conditions anodic oxidation
Ref. 1 5669238; Journal; Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko; CPBTAL;
Chem.Pharm.Bull.; EN; 31; 11; 1983; 4209-4212;
-------------------------

Reaction Details 14 of 77

Reaction Classification Preparation
Reagent CO2-O2, HCl
Catalyst PdCl2-CuCl2
Temperature 25 C
Pressure 18240 Torr
Ref. 1 5737035; Journal; El'man, A. R.; Slivinskii, E. V.; Loktev, S. M.; BACCAT; Bull.Acad.Sci.USSR Div.Chem.Sci.(Engl.Transl.);
EN; 37; 1988; 1969; IASKA6; Izv.Akad.Nauk SSSR Ser.Khim.; RU; 9; 1988; 2188-2189;
-------------------------

Reaction Details 15 of 77

Reaction Classification Preparation
Yield 51 percent Turnov (BRN=105248)
Reagent Zn(MnO4)2/SiO2
Solvent CH2Cl2
Time 0.25 hour(s)
Temperature 20 C
Ref. 1 5738472; Journal; Wolfe, Saul; Ingold, Christopher F.; JACSAT; J.Amer.Chem.Soc.; EN; 105; 26; 1983; 7755-7757;
-------------------------

Reaction Details 16 of 77

Reaction Classification Preparation
Yield 65 percent (BRN=105248)
Reagent RuO4
Solvent CCl4
Time 24 hour(s)
Other Conditions Ambient temperature
Ref. 1 5772763; Journal; Smith, Amos B.; Scarborough, Robert M.; SYNCAV; Synth.Commun.; EN; 10; 3; 1980; 205-212;
-------------------------

Reaction Details 17 of 77

Reaction Classification Chemical behaviour
Reagent H2O, trans-<RuL%1&O2>%2+& (L%1& =
6,7,14,15,16,17,18,19-octahydro-14,18-dimethyl-13H-dibenzo<e,n><1,4,8,12>dioxadiazacyclopentadecine
Solvent trifluoroacetic acid
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.); other object of study: kinetic isotope effect; other conditions: other reagents
Subject Studied Kinetics
Thermodynamic data
Mechanism
Ref. 1 5600408; Journal; Che, Chi-Ming; Tang, Wai-Tong; Wong, Kwok-Yin; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 12; 1991; 3277-3280;
-------------------------

Reaction Details 18 of 77

Reaction Classification Chemical behaviour
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Other Conditions MeCN, p-benzoquinone; other ethers
Subject Studied Product distribution
Mechanism
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
-------------------------

Reaction Details 19 of 77

Reaction Classification Chemical behaviour
Reagent <Ru%V&L(O)>%2+& <HL = <2-hydroxy-2-(pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent HClO4
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.)
Subject Studied Mechanism
Kinetics
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
-------------------------

Reaction Details 20 of 77

Reaction Classification Chemical behaviour
Yield 60 percent Chromat. (BRN=105248)
Reagent tris(acetyloacetonato)Co(III), O2, 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Other Conditions other tetrahydrofuranes; var. $a-diketones; also with Co(II), Fe(III), Ni(II) acetylacetonates
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
-------------------------

Reaction Details 21 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent H2O
Time 10 hour(s)
Temperature 60 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
-------------------------

Reaction Details 22 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CH2Cl2
Time 5 hour(s)
Temperature 35 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 23 of 77

Reaction Classification Preparation
Yield 55 percent (BRN=105248)
Reagent TS-1 (titanium silicate), 30percent H2O2
Time 12 hour(s)
Temperature 70 C
Ref. 1 5994917; Journal; Sasidharan, M.; Suresh, S.; Sudalai, A.; TELEAY; Tetrahedron Lett.; EN; 36; 49; 1995; 9071-9072;
-------------------------

Reaction Details 24 of 77

Reaction Classification Preparation
Yield 33 percent Chromat (BRN=105248)
Reagent aq. t-BuOOH
Catalyst trans-<Ru(H2O)2(bipy)2><PF6>2*H2O
Solvent benzene
Time 5 hour(s)
Other Conditions Ambient temperature
Ref. 1 6009471; Journal; Bailey, Alan J.; Griffith, William P.; Savage, Paul D.; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 21; 1995;
3537-3542;
-------------------------

Reaction Details 25 of 77

Reaction Classification Preparation
Reagent benzil, oxygen
Time 6 hour(s)
Temperature 0 C
Other Conditions Irradiation
Note 1 Yield given
Ref. 1 6045199; Journal; Seto, Hideharu; Yoshida, Keigo; Yoshida, Shigeo; Shimizu, Takeshi; Seki, Hiroshi; Hoshino, Mikio;
TELEAY; Tetrahedron Lett.; EN; 37; 24; 1996; 4179-4182;
-------------------------

Reaction Details 26 of 77

Reaction Classification Preparation
Reagent water
hydrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 27 of 77

Reaction Classification Preparation
Reagent aqueous HNO3
benzene
Temperature 25 C
Ref. 1 605467; Journal; Moschkin; Trudy Sovesc. Vopr. Ispolz. Pentozan. Syria Riga; 1955; 225, 244; Chem.Abstr.; 1959; 15048;
-------------------------

Reaction Details 28 of 77

Reaction Classification Preparation
Reagent water
nitrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 29 of 77

Reaction Classification Preparation
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
-------------------------

Reaction Details 30 of 77

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent ZnCr2O7*3H2O
Solvent CH2Cl2
Time 1.0 hour(s)
Other Conditions Ambient temperature
Ref. 1 5572812; Journal; Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.; SYNTBF; Synthesis; EN; 4; 1986;
285-288;
-------------------------

Reaction Details 31 of 77

Reaction Classification Preparation
Yield 98 percent (BRN=105248)
Reagent trans-<Ru%VI&(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)O2><ClO4>2
Solvent acetonitrile
Time 1 hour(s)
Temperature 25 C
Ref. 1 5541107; Journal; Che, Chi-Ming; Tang, Wai-Tong; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 12; 1990;
3735-3739;
-------------------------

Reaction Details 32 of 77

Reaction Classification Preparation
Yield 80 percent (BRN=105248)
Reagent <Ru%V&L(O)>%2+&-complex <HL = <2-hydroxy-2-(2-pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent acetonitrile
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
-------------------------

Reaction Details 33 of 77

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Catalyst trans-<Ru(VI)(dmpipy)2O2><ClO4>2
Solvent acetonitrile
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5538120; Journal; Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 3; 1991; 379-384;
-------------------------

Reaction Details 34 of 77

Reaction Classification Preparation
Yield 68 percent (BRN=105248)
Reagent Ca(OCl)2
Solvent acetic acid
acetonitrile
H2O
Time 1 hour(s)
Temperature 0 C
Ref. 1 5554344; Journal; Nwaukwa, Stephen O.; Keehn, Philip M.; TELEAY; Tetrahedron Lett.; EN; 23; 1982; 35-38;
-------------------------

Reaction Details 35 of 77

Reaction Classification Preparation
Yield 60 percent Chromat (BRN=105248)
Reagent O2, tris(acetylacetonato)Co(III), 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
-------------------------

Reaction Details 36 of 77

Reaction Classification Preparation
Yield 41 percent (BRN=105248)
Reagent cis-<Ru%VI&(6,6'-Cl2bpy)2O2><ClO4>
Solvent acetonitrile
Time 90 min
Temperature 25 C
Ref. 1 5911524; Journal; Che, Chi-Ming; Leung, Wai-Ho; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 18; 1987; 1376-1377;
-------------------------

Reaction Details 37 of 77

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent Mn2O7
Solvent CCl4
acetone
Temperature -45 C
Ref. 1 5689808; Journal; Troemel, Martin; Russ, Manuel; ANCEAD; Angew.Chem.; GE; 99; 10; 1987; 1037-1038;
-------------------------

Reaction Details 38 of 77

Reaction Classification Preparation
Yield 11 percent (BRN=105248)
Reagent N-hydroxyphthalimide
Solvent pyridine
Other Conditions anodic oxidation
Ref. 1 5669238; Journal; Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko; CPBTAL;
Chem.Pharm.Bull.; EN; 31; 11; 1983; 4209-4212;
-------------------------

Reaction Details 39 of 77

Reaction Classification Preparation
Reagent CO2-O2, HCl
Catalyst PdCl2-CuCl2
Temperature 25 C
Pressure 18240 Torr
Ref. 1 5737035; Journal; El'man, A. R.; Slivinskii, E. V.; Loktev, S. M.; BACCAT; Bull.Acad.Sci.USSR Div.Chem.Sci.(Engl.Transl.);
EN; 37; 1988; 1969; IASKA6; Izv.Akad.Nauk SSSR Ser.Khim.; RU; 9; 1988; 2188-2189;
-------------------------

Reaction Details 40 of 77

Reaction Classification Preparation
Yield 51 percent Turnov (BRN=105248)
Reagent Zn(MnO4)2/SiO2
Solvent CH2Cl2
Time 0.25 hour(s)
Temperature 20 C
Ref. 1 5738472; Journal; Wolfe, Saul; Ingold, Christopher F.; JACSAT; J.Amer.Chem.Soc.; EN; 105; 26; 1983; 7755-7757;
-------------------------

Reaction Details 41 of 77

Reaction Classification Preparation
Yield 65 percent (BRN=105248)
Reagent RuO4
Solvent CCl4
Time 24 hour(s)
Other Conditions Ambient temperature
Ref. 1 5772763; Journal; Smith, Amos B.; Scarborough, Robert M.; SYNCAV; Synth.Commun.; EN; 10; 3; 1980; 205-212;
-------------------------

Reaction Details 42 of 77

Reaction Classification Chemical behaviour
Reagent H2O, trans-<RuL%1&O2>%2+& (L%1& =
6,7,14,15,16,17,18,19-octahydro-14,18-dimethyl-13H-dibenzo<e,n><1,4,8,12>dioxadiazacyclopentadecine
Solvent trifluoroacetic acid
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.); other object of study: kinetic isotope effect; other conditions: other reagents
Subject Studied Kinetics
Thermodynamic data
Mechanism
Ref. 1 5600408; Journal; Che, Chi-Ming; Tang, Wai-Tong; Wong, Kwok-Yin; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 12; 1991; 3277-3280;
-------------------------

Reaction Details 43 of 77

Reaction Classification Chemical behaviour
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Other Conditions MeCN, p-benzoquinone; other ethers
Subject Studied Product distribution
Mechanism
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
-------------------------

Reaction Details 44 of 77

Reaction Classification Chemical behaviour
Reagent <Ru%V&L(O)>%2+& <HL = <2-hydroxy-2-(pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent HClO4
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.)
Subject Studied Mechanism
Kinetics
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
-------------------------

Reaction Details 45 of 77

Reaction Classification Chemical behaviour
Yield 60 percent Chromat. (BRN=105248)
Reagent tris(acetyloacetonato)Co(III), O2, 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Other Conditions other tetrahydrofuranes; var. $a-diketones; also with Co(II), Fe(III), Ni(II) acetylacetonates
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
-------------------------

Reaction Details 46 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent H2O
Time 10 hour(s)
Temperature 60 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
-------------------------

Reaction Details 47 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CH2Cl2
Time 5 hour(s)
Temperature 35 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 48 of 77

Reaction Classification Preparation
Yield 55 percent (BRN=105248)
Reagent TS-1 (titanium silicate), 30percent H2O2
Time 12 hour(s)
Temperature 70 C
Ref. 1 5994917; Journal; Sasidharan, M.; Suresh, S.; Sudalai, A.; TELEAY; Tetrahedron Lett.; EN; 36; 49; 1995; 9071-9072;
-------------------------

Reaction Details 49 of 77

Reaction Classification Preparation
Yield 33 percent Chromat (BRN=105248)
Reagent aq. t-BuOOH
Catalyst trans-<Ru(H2O)2(bipy)2><PF6>2*H2O
Solvent benzene
Time 5 hour(s)
Other Conditions Ambient temperature
Ref. 1 6009471; Journal; Bailey, Alan J.; Griffith, William P.; Savage, Paul D.; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 21; 1995;
3537-3542;
-------------------------

Reaction Details 50 of 77

Reaction Classification Preparation
Reagent benzil, oxygen
Time 6 hour(s)
Temperature 0 C
Other Conditions Irradiation
Note 1 Yield given
Ref. 1 6045199; Journal; Seto, Hideharu; Yoshida, Keigo; Yoshida, Shigeo; Shimizu, Takeshi; Seki, Hiroshi; Hoshino, Mikio;
TELEAY; Tetrahedron Lett.; EN; 37; 24; 1996; 4179-4182;
-------------------------

Reaction Details 51 of 77

Reaction Classification Preparation
Yield 68 percent (BRN=105248)
Reagent NaBrO3
NaHSO3
Solvent H2O
Time 16.25 hour(s)
Temperature 20 C
Reaction Type Oxidation
Ref. 1 6148927; Journal; Sakaguchi, Satoshi; Kikuchi, Daisuke; Ishii, Yasutaka; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 70; 10; 1997;
2561 - 2566;
-------------------------

Reaction Details 52 of 77

Reaction Classification Preparation
Reagent water
hydrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 53 of 77

Reaction Classification Preparation
Reagent aqueous HNO3
benzene
Temperature 25 C
Ref. 1 605467; Journal; Moschkin; Trudy Sovesc. Vopr. Ispolz. Pentozan. Syria Riga; 1955; 225, 244; Chem.Abstr.; 1959; 15048;
-------------------------

Reaction Details 54 of 77

Reaction Classification Preparation
Reagent water
nitrogen
Temperature 280 C
Pressure 147101.6 Torr
Other Conditions beim Behandeln mit einem Kupferoxid-Chromoxid-Katalysator
Ref. 1 605466; Patent; BASF; DE 849104; 1950; DRP/DRBP Org.Chem.; DE; GE;
-------------------------

Reaction Details 55 of 77

Reaction Classification Preparation
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
-------------------------

Reaction Details 56 of 77

Reaction Classification Preparation
Yield 70 percent (BRN=105248)
Reagent ZnCr2O7*3H2O
Solvent CH2Cl2
Time 1.0 hour(s)
Other Conditions Ambient temperature
Ref. 1 5572812; Journal; Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.; SYNTBF; Synthesis; EN; 4; 1986;
285-288;
-------------------------

Reaction Details 57 of 77

Reaction Classification Preparation
Yield 98 percent (BRN=105248)
Reagent trans-<Ru%VI&(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)O2><ClO4>2
Solvent acetonitrile
Time 1 hour(s)
Temperature 25 C
Ref. 1 5541107; Journal; Che, Chi-Ming; Tang, Wai-Tong; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 12; 1990;
3735-3739;
-------------------------

Reaction Details 58 of 77

Reaction Classification Preparation
Yield 80 percent (BRN=105248)
Reagent <Ru%V&L(O)>%2+&-complex <HL = <2-hydroxy-2-(2-pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent acetonitrile
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
-------------------------

Reaction Details 59 of 77

Reaction Classification Preparation
Yield 85 percent (BRN=105248)
Catalyst trans-<Ru(VI)(dmpipy)2O2><ClO4>2
Solvent acetonitrile
Time 4 hour(s)
Other Conditions Ambient temperature
Ref. 1 5538120; Journal; Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 3; 1991; 379-384;
-------------------------

Reaction Details 60 of 77

Reaction Classification Preparation
Yield 68 percent (BRN=105248)
Reagent Ca(OCl)2
Solvent acetic acid
acetonitrile
H2O
Time 1 hour(s)
Temperature 0 C
Ref. 1 5554344; Journal; Nwaukwa, Stephen O.; Keehn, Philip M.; TELEAY; Tetrahedron Lett.; EN; 23; 1982; 35-38;
-------------------------

Reaction Details 61 of 77

Reaction Classification Preparation
Yield 60 percent Chromat (BRN=105248)
Reagent O2, tris(acetylacetonato)Co(III), 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
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Reaction Details 62 of 77

Reaction Classification Preparation
Yield 41 percent (BRN=105248)
Reagent cis-<Ru%VI&(6,6'-Cl2bpy)2O2><ClO4>
Solvent acetonitrile
Time 90 min
Temperature 25 C
Ref. 1 5911524; Journal; Che, Chi-Ming; Leung, Wai-Ho; JCCCAT; J.Chem.Soc.Chem.Commun.; EN; 18; 1987; 1376-1377;
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Reaction Details 63 of 77

Reaction Classification Preparation
Yield 86 percent (BRN=105248)
Reagent Mn2O7
Solvent CCl4
acetone
Temperature -45 C
Ref. 1 5689808; Journal; Troemel, Martin; Russ, Manuel; ANCEAD; Angew.Chem.; GE; 99; 10; 1987; 1037-1038;
-------------------------

Reaction Details 64 of 77

Reaction Classification Preparation
Yield 11 percent (BRN=105248)
Reagent N-hydroxyphthalimide
Solvent pyridine
Other Conditions anodic oxidation
Ref. 1 5669238; Journal; Masui, Masaichiro; Hara, Seijiro; Ueshima, Takahiro; Kawaguchi, Tetsuo; Ozaki, Shigeko; CPBTAL;
Chem.Pharm.Bull.; EN; 31; 11; 1983; 4209-4212;
-------------------------

Reaction Details 65 of 77

Reaction Classification Preparation
Reagent CO2-O2, HCl
Catalyst PdCl2-CuCl2
Temperature 25 C
Pressure 18240 Torr
Ref. 1 5737035; Journal; El'man, A. R.; Slivinskii, E. V.; Loktev, S. M.; BACCAT; Bull.Acad.Sci.USSR Div.Chem.Sci.(Engl.Transl.);
EN; 37; 1988; 1969; IASKA6; Izv.Akad.Nauk SSSR Ser.Khim.; RU; 9; 1988; 2188-2189;
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Reaction Details 66 of 77

Reaction Classification Preparation
Yield 51 percent Turnov (BRN=105248)
Reagent Zn(MnO4)2/SiO2
Solvent CH2Cl2
Time 0.25 hour(s)
Temperature 20 C
Ref. 1 5738472; Journal; Wolfe, Saul; Ingold, Christopher F.; JACSAT; J.Amer.Chem.Soc.; EN; 105; 26; 1983; 7755-7757;
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Reaction Details 67 of 77

Reaction Classification Preparation
Yield 65 percent (BRN=105248)
Reagent RuO4
Solvent CCl4
Time 24 hour(s)
Other Conditions Ambient temperature
Ref. 1 5772763; Journal; Smith, Amos B.; Scarborough, Robert M.; SYNCAV; Synth.Commun.; EN; 10; 3; 1980; 205-212;
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Reaction Details 68 of 77

Reaction Classification Chemical behaviour
Reagent H2O, trans-<RuL%1&O2>%2+& (L%1& =
6,7,14,15,16,17,18,19-octahydro-14,18-dimethyl-13H-dibenzo<e,n><1,4,8,12>dioxadiazacyclopentadecine
Solvent trifluoroacetic acid
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.); other object of study: kinetic isotope effect; other conditions: other reagents
Subject Studied Kinetics
Thermodynamic data
Mechanism
Ref. 1 5600408; Journal; Che, Chi-Ming; Tang, Wai-Tong; Wong, Kwok-Yin; Li, Chi-Keung; JCDTBI; J.Chem.Soc.Dalton Trans.;
EN; 12; 1991; 3277-3280;
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Reaction Details 69 of 77

Reaction Classification Chemical behaviour
Yield 34 percent (BRN=105248)
Reagent H3PO5
Time 2 hour(s)
Temperature 25 C
Other Conditions MeCN, p-benzoquinone; other ethers
Subject Studied Product distribution
Mechanism
Ref. 1 5561643; Journal; Ogata, Yoshiro; Tomizawa, Kohtaro; Ikeda, Toshiyuki; JOCEAH; J.Org.Chem.; EN; 45; 7; 1980;
1320-1322;
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Reaction Details 70 of 77

Reaction Classification Chemical behaviour
Reagent <Ru%V&L(O)>%2+& <HL = <2-hydroxy-2-(pyridyl)ethyl>bis<2-(2-pyridyl)ethyl>amine>
Solvent HClO4
Temperature 24.9 C
Other Conditions $DH(excit.), $DS(excit.)
Subject Studied Mechanism
Kinetics
Ref. 1 5582759; Journal; Che, Chi-Ming; Ho, Clare; Lau, Tai-Chu; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 5; 1991; 1259-1263;
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Reaction Details 71 of 77

Reaction Classification Chemical behaviour
Yield 60 percent Chromat. (BRN=105248)
Reagent tris(acetyloacetonato)Co(III), O2, 2,3-butanedione
Time 6 hour(s)
Temperature 50 C
Pressure 760 Torr
Other Conditions other tetrahydrofuranes; var. $a-diketones; also with Co(II), Fe(III), Ni(II) acetylacetonates
Ref. 1 5849077; Journal; Hata, Eiichiro; Takai, Toshihiro; Mukaiyama, Teruaki; CMLTAG; Chem.Lett.; EN; 9; 1993; 1513-1516;
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Reaction Details 72 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent benzyltrimethylammonium tribromide, Na2HPO4
Solvent H2O
Time 10 hour(s)
Temperature 60 C
Ref. 1 5936936; Journal; Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 62; 8; 1989;
2585-2588;
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Reaction Details 73 of 77

Reaction Classification Preparation
Yield 67 percent (BRN=105248)
Reagent aq. sodium bromate
Catalyst 47percent hydrobromic acid
Solvent CH2Cl2
Time 5 hour(s)
Temperature 35 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;
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Reaction Details 74 of 77

Reaction Classification Preparation
Yield 55 percent (BRN=105248)
Reagent TS-1 (titanium silicate), 30percent H2O2
Time 12 hour(s)
Temperature 70 C
Ref. 1 5994917; Journal; Sasidharan, M.; Suresh, S.; Sudalai, A.; TELEAY; Tetrahedron Lett.; EN; 36; 49; 1995; 9071-9072;
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Reaction Details 75 of 77

Reaction Classification Preparation
Yield 33 percent Chromat (BRN=105248)
Reagent aq. t-BuOOH
Catalyst trans-<Ru(H2O)2(bipy)2><PF6>2*H2O
Solvent benzene
Time 5 hour(s)
Other Conditions Ambient temperature
Ref. 1 6009471; Journal; Bailey, Alan J.; Griffith, William P.; Savage, Paul D.; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 21; 1995;
3537-3542;
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Reaction Details 76 of 77

Reaction Classification Preparation
Reagent benzil, oxygen
Time 6 hour(s)
Temperature 0 C
Other Conditions Irradiation
Note 1 Yield given
Ref. 1 6045199; Journal; Seto, Hideharu; Yoshida, Keigo; Yoshida, Shigeo; Shimizu, Takeshi; Seki, Hiroshi; Hoshino, Mikio;
TELEAY; Tetrahedron Lett.; EN; 37; 24; 1996; 4179-4182;
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Reaction Details 77 of 77

Reaction Classification Preparation
Yield 68 percent (BRN=105248)
Reagent NaBrO3
NaHSO3
Solvent H2O
Time 16.25 hour(s)
Temperature 20 C
Reaction Type Oxidation
Ref. 1 6178927; Journal; Sakaguchi, Satoshi; Kikuchi, Daisuke; Ishii, Yasutaka; BCSJA8; Bull.Chem.Soc.Jpn.; EN; 70; 10; 1997;
2561 - 2566;

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Ipsa scientia potestas est
