e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Journal of Organic Chemistry

A method for mild photochemical oxidation; conversion of phenacyl sulfides into carbonyl compounds

E Vedejs, DA Perry

Index: Vedejs, E.; Perry, D. A. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 573 - 575

Full Text: HTML

Citation Number: 27

Abstract

Summary: Sunlamp irradiation of phenacyl sulfides PhCOCH2SCHRR'affords thiocarbonyl compounds S= CRR'that can be trapped in high yield by using the nitronate CH, CH= N+(OTBS) O-; the heterocycle 3 resulting from 1, 3-dipolar cycloaddition is cleaved rapidly by fluoride ion to give ketones or aldehydes.

cyclododecanethiol Structure

cyclododecanethiol

2-Chloroacetophenone Structure

2-Chloroacetophenone

~%

2-cyclododecylsulfanyl-1-phenylethanone Structure

2-cyclododecyls...

N/A Structure

2-Chloroacetophenone Structure

2-Chloroacetophenone

~%

(2-phenacylsulfanylcyclohexyl) acetate Structure

(2-phenacylsulf...

2-(acetylthio)-1-phenylethyl acetate Structure

2-(acetylthio)-...

2-Chloroacetophenone Structure

2-Chloroacetophenone

~%

(2-phenacylsulfanyl-1-phenylethyl) acetate Structure

(2-phenacylsulf...

ACETYLTHIOACETOPHENONE Structure

ACETYLTHIOACETO...

~%

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

2-Chloroacetophenone Structure

2-Chloroacetophenone

~%

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

cyclohexenone Structure

2-Mercapto-1-phenylethanone Structure

2-Mercapto-1-ph...

~%

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

ACETYLTHIOACETOPHENONE Structure

ACETYLTHIOACETO...

~%

2-methyl-5-phenacylsulfanylnonan-3-one Structure

2-methyl-5-phen...

2-Chloroacetophenone Structure

2-Chloroacetophenone

~%

2-methyl-5-phenacylsulfanylnonan-3-one Structure

2-methyl-5-phen...

N/A Structure

2-Mercapto-1-phenylethanone Structure

2-Mercapto-1-ph...

~%

2-methyl-5-phenacylsulfanylnonan-3-one Structure

2-methyl-5-phen...

N/A Structure

~%

2-acetyl-3-phenylmethoxybutanal Structure

2-acetyl-3-phen...

(1-phenacylsulfanyl-3-phenylmethoxybutan-2-yl) acetate Structure

(1-phenacylsulf...

~%

2-acetyl-3-phenylmethoxybutanal Structure

2-acetyl-3-phen...

1-(5-butyl-2-((tert-butyldimethylsilyl)oxy)-3-methyl-1,4,2-oxathiazolidin-5-yl)-3-methylbutan-2-one Structure

1-(5-butyl-2-((...

~58%

2-methylnonane-3,5-dione Structure

2-methylnonane-...

N/A Structure

~%

2-methylnonane-3,5-dione Structure

2-methylnonane-...

2-methyl-5-phenacylsulfanylnonan-3-one Structure

2-methyl-5-phen...

~%

2-methylnonane-3,5-dione Structure

2-methylnonane-...

cyclohexenone Structure

~%

3-methylsulfanylcyclohex-2-en-1-one Structure

3-methylsulfany...

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

~%

3-methylsulfanylcyclohex-2-en-1-one Structure

3-methylsulfany...

3-sulfanylcyclohex-2-en-1-one Structure

3-sulfanylcyclo...

methyl iodide Structure

~%

3-methylsulfanylcyclohex-2-en-1-one Structure

3-methylsulfany...

2-((tert-butyldimethylsilyl)oxy)-3-methyl-1-oxa-4-thia-2-azaspiro[4.5]decan-6-yl acetate Structure

2-((tert-butyld...

~%

2-OXOCYCLOHEXYL ACETATE Structure

2-OXOCYCLOHEXYL...

N/A Structure

~%

2-OXOCYCLOHEXYL ACETATE Structure

2-OXOCYCLOHEXYL...

(2-phenacylsulfanylcyclohexyl) acetate Structure

(2-phenacylsulf...

~%

2-OXOCYCLOHEXYL ACETATE Structure

2-OXOCYCLOHEXYL...

2-((tert-butyldimethylsilyl)oxy)-3-methyl-1-oxa-4-thia-2-azaspiro[4.5]decan-7-one Structure

2-((tert-butyld...

~%

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

~%

1,3-Cyclohexanedione Structure

1,3-Cyclohexanedione

3-phenylpropane-1-thiol Structure

3-phenylpropane...

~%

3-methyl-5-(2-phenylethyl)-1,4,2-oxathiazole Structure

3-methyl-5-(2-p...

1-phenyl-2-(3-phenylpropylsulfanyl)ethanone Structure

1-phenyl-2-(3-p...

~%

3-methyl-5-(2-phenylethyl)-1,4,2-oxathiazole Structure

3-methyl-5-(2-p...

2-((tert-butyldimethylsilyl)oxy)-3-methyl-5-phenethyl-1,4,2-oxathiazolidine Structure

2-((tert-butyld...

~%

3-Phenylpropanal Structure

3-Phenylpropanal

3-methyl-5-(2-phenylethyl)-1,4,2-oxathiazole Structure

3-methyl-5-(2-p...

3-phenacylsulfanylcyclohexan-1-one Structure

3-phenacylsulfa...

~%

3-sulfanylcyclohex-2-en-1-one Structure

3-sulfanylcyclo...

cyclohexenone Structure

~%

3-sulfanylcyclohex-2-en-1-one Structure

3-sulfanylcyclo...