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

The Journal of Organic Chemistry

Reactions of (aryloxy) oxosulfonium ylides with carbonyl compounds

K Okuma, K Nakanishi, H Ohta

Index: Okuma, Kentaro; Nakanishi, Kazuto; Ohta, Hiroshi Journal of Organic Chemistry, 1984 , vol. 49, p. 1402 - 1407

Full Text: HTML

Citation Number: 20

Abstract

Reactions of (ary1oxy) oxosulfonium salts with alkyllithium followed by the addition of carbonyl compounds gave 0-aryloxy sulfones,/3-aroyloxy sulfones, and a,@-unsaturated or p, y-unsaturated sulfones in 1.4-17.9%, 1.2-7.2%, and 4.5-13.5% yields, respectively. Ylides obtained by treatment of these sulfonium salts with n-BuLi reacted with carbonyl compounds to give betaines, which formed unusual four-membered cyclic alkoxyoxosulfonium salts. ...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

(4-Chlorophenoxy)dimethylsulfoxonium Tetrafluoroborate Structure

(4-Chlorophenox...

~%

Dimethyl sulfone Structure

Dimethyl sulfone

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Structure

~19%

Dimethyl sulfone Structure

Dimethyl sulfone

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

Detail

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Structure

~5%

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

1-chloro-4-[1-(4-chlorophenoxy)-2-methylsulfonylethyl]benzene Structure

1-chloro-4-[1-(...

Detail

methyl p-tolyl methanesulfinate Structure

methyl p-tolyl ...

Benzaldehyde Structure

~9%

p-Cresol Structure

Dimethyl sulfone Structure

Dimethyl sulfone

Detail

methyl p-tolyl methanesulfinate Structure

methyl p-tolyl ...

Benzaldehyde Structure

~1%

p-Cresol Structure

Dimethyl sulfone Structure

Dimethyl sulfone

Detail

N/A Structure

Benzaldehyde Structure

~0%

N-ethyl-N-(4-methylphenyl)methanesulfonamide Structure

N-ethyl-N-(4-me...

N-Ethyl-N-tolyl-2-(p-chlorophenoxy)-2-phenylethanesulfonamide Structure

N-Ethyl-N-tolyl...

Detail

Benzophenone Structure

N/A Structure

~%

N-ethyl-N-(4-methylphenyl)methanesulfonamide Structure

N-ethyl-N-(4-me...

4-Chlorophenol Structure

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Structure

~15%

Dimethyl sulfone Structure

Dimethyl sulfone

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

Detail

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Structure

~5%

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

1-chloro-4-[1-(4-chlorophenoxy)-2-methylsulfonylethyl]benzene Structure

1-chloro-4-[1-(...

Detail

Benzophenone Structure

Structure

~0%

Dimethyl sulfone Structure

Dimethyl sulfone

4-Chlorophenol Structure

p-Tolualdehyde Structure

Structure

~15%

Dimethyl sulfone Structure

Dimethyl sulfone

1-[1-(4-chlorophenoxy)-2-methylsulfonylethyl]-4-methylbenzene Structure

1-[1-(4-chlorop...

Detail

1-chloro-4-(2-methylsulfonyl-1-phenylethoxy)benzene Structure

1-chloro-4-(2-m...

~%

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

Benzaldehyde Structure

(4-Chlorophenoxy)dimethylsulfoxonium Tetrafluoroborate Structure

(4-Chlorophenox...

~%

Dimethyl sulfone Structure

Dimethyl sulfone

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

methyl p-tolyl methanesulfinate Structure

methyl p-tolyl ...

Benzaldehyde Structure

~20%

p-Cresol Structure

Dimethyl sulfone Structure

Dimethyl sulfone

Detail

Structure

Benzaldehyde Structure

~27%

Dimethyl sulfone Structure

Dimethyl sulfone

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

Detail

Structure

Benzaldehyde Structure

~5%

Dimethyl sulfone Structure

Dimethyl sulfone

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

Detail

methyl p-tolyl methanesulfinate Structure

methyl p-tolyl ...

Benzaldehyde Structure

~5%

p-Cresol Structure

Dimethyl sulfone Structure

Dimethyl sulfone

Detail

(4-Chlorophenoxy)dimethylsulfoxonium Tetrafluoroborate Structure

(4-Chlorophenox...

4-tert-Butylcyclohexanone Structure

4-tert-Butylcyc...

~%

4-tert-butyl-1-(methylsulfonylmethyl)cyclohexene Structure

4-tert-butyl-1-...

Structure

4-tert-Butylcyclohexanone Structure

4-tert-Butylcyc...

~41%

Dimethyl sulfone Structure

Dimethyl sulfone

4-tert-butyl-1-(methylsulfonylmethyl)cyclohexene Structure

4-tert-butyl-1-...

Detail

Structure

Benzaldehyde Structure

~22%

Dimethyl sulfone Structure

Dimethyl sulfone

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

Detail

Structure

Benzaldehyde Structure

~4%

Dimethyl sulfone Structure

Dimethyl sulfone

(E)-(2-(Methylsulfonyl)ethenyl)benzene Structure

(E)-(2-(Methyls...

Detail

Benzophenone Structure

Structure

~72%

Dimethyl sulfone Structure

Dimethyl sulfone

4-Chlorophenol Structure

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Structure

~1%

Benzene, 1-chloro-4-[(2-(methylsulfonyl)ethenyl]- Structure

Benzene, 1-chlo...

1-chloro-4-[1-(4-chlorophenoxy)-2-methylsulfonylethyl]benzene Structure

1-chloro-4-[1-(...

Detail