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Conditions | Yield |
---|---|
With ethyl phosphinate In ethanol other reagent; | 100% |
With ethyl phosphinate In ethanol Product distribution; other reagent; | 100% |
With tungsten(VI) chloride; sodium iodide In acetonitrile for 1.5h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With pyridine chromium peroxide for 0.1h; Product distribution; effect of various chromium(VI) based oxidants; | 100% |
With bis(tetra-n-butylammonium) tetrakis(benzenethiolato-μ3-sulfidoiron); oxygen In acetonitrile at 0℃; for 0.166667h; other iron-sulfur complex or other iron compounds as the catalyst in reaction oxidation; | 100% |
With barium ferrate(VI) In benzene for 0.25h; Product distribution; Heating; | 100% |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | 100% |
With tungsten(VI) chloride; sodium iodide In acetonitrile for 16h; Ambient temperature; | 97% |
With Silphos; iodine In acetonitrile for 10h; Heating; | 96% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol | A 100% B 61% |
Conditions | Yield |
---|---|
With (2,2,4,4-tetrafluoropropoxy)tellurane In diethyl ether at -50 - -40℃; for 0.166667h; | A 100% B n/a |
Perbenzoic acid
bis-benzenesulfenyl-amine
A
benzoic acid phenyl ester
B
biphenyl
C
benzoic acid
D
diphenyldisulfane
Conditions | Yield |
---|---|
In benzene Kinetics; Product distribution; Mechanism; isotopic effect, effect of benzoic acid and styrene on the reaction; | A 1.4% B 0.2% C 100% D 50% E n/a |
Conditions | Yield |
---|---|
With ethanol In dichloromethane CH2Cl2 soln. of reagents was stirred at 0°C for 1 h under N2; concd., chromd. on silica gel with hexane-ethyl acetate; | A 100% B n/a |
Conditions | Yield |
---|---|
In dichloromethane CH2Cl2, 0°C, 1 h; | A 100% B n/a |
thiophenol
[(trifluoroacetyl)imino]tris-(2-methylphenyl)-λ(5)-bismuthane
A
tri-o-tolylbismuth
B
diphenyldisulfane
Conditions | Yield |
---|---|
In benzene room temp., 3 h; | A 100% B 80% |
N-benzylidene-S-phenylthiohydroxylamine
diphenyldisulfane
Conditions | Yield |
---|---|
With oxygen; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 3h; | 100% |
Benzoyl bromide
thallium thiophenoxide
A
phenyl thiobenzoate
B
diphenyldisulfane
Conditions | Yield |
---|---|
In diethyl ether for 0.5h; | A 99% B 1% |
p-(1-methyl-1-nitropropyl)nitrobenzene
sodium thiophenolate
A
2-(p-nitrophenyl)-2-butyl phenyl sulfide
B
diphenyldisulfane
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 0.75h; | A 99% B 99% |
thallium thiophenoxide
benzoyl chloride
A
phenyl thiobenzoate
B
diphenyldisulfane
Conditions | Yield |
---|---|
In diethyl ether for 1h; | A 99% B 1% |
diphenyl-N-(p-toluenesulfonyl)selenimide
thiophenol
A
diphenylselenide
B
toluene-4-sulfonamide
C
diphenyldisulfane
Conditions | Yield |
---|---|
In chloroform for 0.25h; Product distribution; Ambient temperature; | A 96% B 99% C 97% |
N-(p-tolylsulfonyl)dibenzylselenimide
thiophenol
A
dibenzyl selenide
B
toluene-4-sulfonamide
C
diphenyldisulfane
Conditions | Yield |
---|---|
In chloroform for 0.166667h; Product distribution; Ambient temperature; | A 98% B 99% C 97% |
triphenyl bismuth (2+); dichloride
thiophenol
diphenyldisulfane
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 60℃; for 18h; | 99% |
thallium thiophenoxide
acetyl chloride
A
S-phenyl thioacetate
B
diphenyldisulfane
Conditions | Yield |
---|---|
In diethyl ether for 0.5h; | A 99% B 1% |
diphenyldisulfane
Conditions | Yield |
---|---|
With sulfur In N,N-dimethyl-formamide at 130℃; for 5.5h; Substitution; | 99% |
A
biphenyl
B
diphenyl sulfide
C
triphenylantimony
D
diphenyldisulfane
E
benzene
Conditions | Yield |
---|---|
In neat (no solvent) thermal decompn. of Sb compd. in a sealed tube on heating to 140°C for 3 h; not isolated, detected by GLC and TLC; | A 21% B 69% C 99% D 30% E 6% |
9-bromophenanthrene
S-phenyl tert-butylcarbamothioate
A
N-(tert-butyl)phenanthrene-9-carboxamide
B
diphenyldisulfane
Conditions | Yield |
---|---|
Stage #1: 9-bromophenanthrene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: S-phenyl tert-butylcarbamothioate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h; | A 76% B 99% |
1-Bromo-2,4,6-triisopropylbenzene
B
diphenyldisulfane
Conditions | Yield |
---|---|
Stage #1: 2,4,6-triisopropyl-1-bromobenzene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: S-phenyl (1-adamantyl)thiocarbamate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h; Schlenk technique; | A 98% B 99% |
1-bromo-4-tert-butylbenzene
A
N-(1-adamantyl)-4-(tert-butyl)benzamide
B
diphenyldisulfane
Conditions | Yield |
---|---|
Stage #1: 1-bromo-4-tert-butylbenzene With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: S-phenyl (1-adamantyl)thiocarbamate In 2-methyltetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #3: With ammonium hydroxide; oxygen In 2-methyltetrahydrofuran; water under 760.051 Torr; for 18h; Schlenk technique; | A 86% B 99% |
Conditions | Yield |
---|---|
With iodine; triphenylphosphine In water at 100℃; Green chemistry; | 98% |
With tungsten(VI) chloride; sodium iodide In acetonitrile for 12h; Ambient temperature; | 95% |
With Silphos; iodine In acetonitrile for 12h; Heating; | 95% |
chloro-trimethyl-silane
thallium thiophenoxide
A
phenylthiotrimethylsilane
B
diphenyldisulfane
Conditions | Yield |
---|---|
In diethyl ether for 18h; | A 98% B 2% |
Conditions | Yield |
---|---|
With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate; basolite C300 In water; N,N-dimethyl-formamide at 130℃; for 6h; Green chemistry; | 98% |
With sulfur; potassium hydroxide In water at 130℃; for 7.5h; Green chemistry; | 95% |
With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 15h; | 93% |
2-[(1-phenylmethyl)sulfinyl]pyridine
A
2-Benzylpyridine
B
S-Phenyl benzenethiosulfonate
C
S-phenyl benzenethiosulfinate
D
diphenyldisulfane
Conditions | Yield |
---|---|
In tetrahydrofuran Product distribution; Mechanism; Ambient temperature; investigation of reaction with various Grignard reagents and n-BuLi; | A 98% B 3% C 60% D 16% |
In tetrahydrofuran Ambient temperature; | A 98% B 3% C 60% D 16% |
2-[(1-phenylmethyl)sulfinyl]pyridine
A
2-Benzylpyridine
B
S-Phenyl benzenethiosulfonate
C
S-phenyl benzenethiosulfinate
D
diphenyldisulfane
Conditions | Yield |
---|---|
With phenylmagnesium bromide In tetrahydrofuran Ambient temperature; | A 98% B 3% C 60% D 16% |
With phenylmagnesium bromide In tetrahydrofuran Ambient temperature; | A 98% B 3% C 60% D 16% |
Acetyl bromide
thallium thiophenoxide
A
S-phenyl thioacetate
B
diphenyldisulfane
Conditions | Yield |
---|---|
In diethyl ether for 1h; | A 98% B 1% |
α-naphthol
4'-nitrobenzenesulfenanilide
A
2-phenylthio-1-naphthol
B
4-(phenylthio)naphthalen-1-ol
C
4-nitro-aniline
D
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given; | A 42% B 33% C 98% D 14% |
α-naphthol
4'-nitrobenzenesulfenanilide
A
2-phenylthio-1-naphthol
B
4-(phenylthio)naphthalen-1-ol
C
4-nitro-aniline
D
2,4-bis(phenylthio)naphthalen-1-ol
E
diphenyldisulfane
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 0.166667h; Product distribution; Mechanism; 1.5 eqiv. TFA; | A 42% B 33% C 98% D 10% E 14% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; methanol for 2h; Heating; | 100% |
With sodium tetrahydroborate In tetrahydrofuran; methanol for 2h; Heating; solvent effect (t-BuOH, DME, 1,4-dioxane, EtOH); | 100% |
With sodium diethylpiperidinohydroaluminate In tetrahydrofuran at 0℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With chlorine In dichloromethane at 0℃; for 0.333333h; | 100% |
With (Dichloroiodo)benzene In dichloromethane at 20℃; for 0.333333h; | 95% |
With chlorine In tetrachloromethane at -78℃; | 93% |
Conditions | Yield |
---|---|
With sulfuryl dichloride; acetic acid at -40℃; for 3h; | 100% |
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 5.3h; | 85% |
With sulfuryl dichloride; acetic acid at -20 - 35℃; for 6h; | 85% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Heating; | 100% |
With dipotassium peroxodisulfate In trifluoroacetic acid at 20℃; for 16h; | 89% |
Stage #1: diphenyldisulfane With thionyl chloride In 1,2-dichloro-ethane at 5 - 30℃; for 4h; Stage #2: With aluminum (III) chloride In 1,2-dichloro-ethane at 5 - 10℃; for 1h; Stage #3: methoxybenzene In 1,2-dichloro-ethane for 4h; | 88.5% |
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Product distribution; Heating; effect of Lewis acid and silver salt; |
1-chloro-2,4-dinitro-benzene
diphenyldisulfane
2,4-dinitro-1-phenylsulfanyl-benzene
Conditions | Yield |
---|---|
With borax; N-Acetylcysteine In methanol; water for 1h; Ambient temperature; | 100% |
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonim bromide In tetrahydrofuran; water for 4h; Product distribution; Heating; | 95% |
With sodium hydroxide; cetyltrimethylammonim bromide; Aminoiminomethanesulfinic acid In tetrahydrofuran for 4h; Heating; | 95% |
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonim bromide In tetrahydrofuran; water for 4h; Heating; | 95% |
With aluminium trichloride; zinc In water; N,N-dimethyl-formamide at 65℃; for 6h; | 95% |
Conditions | Yield |
---|---|
at 230 - 270℃; for 8h; Mechanism; other aryl iodides; | 100% |
at 230 - 270℃; for 8h; | 100% |
With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h; other pressures and times; var. prim. and sec. alcohols; | 100% |
With tributylphosphine In tetrahydrofuran at 62℃; under 7500600 Torr; for 3h; | 100% |
2-methylmethoxybenzene
diphenyldisulfane
1-methoxy-2-methyl-4-(phenylsulfanyl)benzene
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; antimonypentachloride In 1,2-dichloro-ethane for 3h; Heating; | 100% |
methyl (R)-3-hydroxy-2-methylpropionate
diphenyldisulfane
(S)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester
Conditions | Yield |
---|---|
With tributylphosphine In acetonitrile for 4.5h; Ambient temperature; | 100% |
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; | 95% |
Conditions | Yield |
---|---|
In benzene at 35 - 45℃; for 4h; Irradiation; | 100% |
<(E)-3,3-dimethyl-1-butenyl>mercuric chloride
diphenyldisulfane
E-3,3-Dimethylbut-1-en-1-yl-phenylsulfid
Conditions | Yield |
---|---|
In benzene at 35 - 45℃; for 6h; Irradiation; | 100% |
2-[1,3]Dioxolan-2-ylmethyl-3,3-dimethyl-butan-1-ol
diphenyldisulfane
2-(3,3-Dimethyl-2-phenylsulfanylmethyl-butyl)-[1,3]dioxolane
Conditions | Yield |
---|---|
With pyridine; tributylphosphine at 25℃; | 100% |
5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione
diphenyldisulfane
5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -70℃; | 100% |
2-(2-(but-3-yn-1-yl)-1,3-dioxolan-2-yl)ethan-1-ol
diphenyldisulfane
2-(3-butynyl)-2-<2-(phenylthio)ethyl>-1,3-dioxolane
Conditions | Yield |
---|---|
With tributylphosphine In benzene for 0.5h; | 100% |
diphenyldisulfane
1-ethoxymethyl-5-lithio-2-phenylthioimidazole
1-ethoxymethyl-2,5-bis(phenylthio)imidazole
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -70℃; | 100% |
With n-butyllithium In tetrahydrofuran at -78℃; | 100% |
diphenyldisulfane
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
1,2:3,4-di-O-isopropylidene-6-S-phenyl-6-thio-α-D-galactopyranoside
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran at 62℃; under 10000 Torr; for 5h; | 100% |
With tributylphosphine In pyridine at 20℃; for 24h; | 96% |
With pyridine; tributylphosphine for 20h; Ambient temperature; | 95% |
With tributylphosphine In pyridine for 12h; Ambient temperature; | 86% |
diphenyldisulfane
(E)-5-[(2R,3R)-3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranyl]-2-methyl-pent-2-en-1-ol
(2R,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((E)-4-methyl-5-phenylsulfanyl-pent-3-enyl)-oxirane
Conditions | Yield |
---|---|
With tributylphosphine In dichloromethane for 0.5h; Ambient temperature; | 100% |
diphenyldisulfane
(Z)-6-(1-Methylcyclohexa-2,5-dienyl)hex-5-en-1-ol
3-Methyl-3-[(Z)-6-(phenylsulfenyl)hex-1-enyl]cyclohexa-1,4-diene
Conditions | Yield |
---|---|
With pyridine; tributylphosphine | 100% |
With tributylphosphine In pyridine at 20℃; for 7h; Substitution; | 100% |
3-hydroxy-(2S)-methylpropionate
diphenyldisulfane
(R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran at 20℃; for 24h; | 100% |
With tributylphosphine In tetrahydrofuran for 24h; Ambient temperature; | 99% |
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; | 85% |
With tributylphosphine In N,N-dimethyl-formamide at 0 - 25℃; for 5h; Yield given; |
diphenyldisulfane
(1S,2R,3R)-1-acetoxymethyl-2-hydroxymethyl-3-phenylcyclopropane
Acetic acid (1S,2S,3R)-2-phenyl-3-phenylsulfanylmethyl-cyclopropylmethyl ester
Conditions | Yield |
---|---|
With tributylphosphine In pyridine at 20℃; for 1h; | 100% |
With tributylphosphine In pyridine at 20℃; Substitution; |
(+/-)-(2R,3R)-2,3-epoxy-1-nonanol
diphenyldisulfane
Conditions | Yield |
---|---|
With tributylphosphine In pyridine at 0℃; | 100% |
diphenyldisulfane
(2S)-2-vinyl-3-phenyl-1-propanol
Conditions | Yield |
---|---|
With tributylphosphine In pyridine at 20℃; for 1h; | 100% |
diphenyldisulfane
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane
Conditions | Yield |
---|---|
With tributylphosphine In pyridine at 20℃; for 24h; | 100% |
cyclopentadecanone oxime
diphenyldisulfane
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran at 20℃; | 100% |
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