The Journal of Organic Chemistry

Nucleophilic displacements alpha to sulfonyl groupings

FG Bordwell, BB Jarvis

Index: Bordwell,F.G.; Jarvis,B.B. Journal of Organic Chemistry, 1968 , vol. 33, # 3 p. 1182 - 1185

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Citation Number: 43

Abstract

The reaction of bromomethyl p-tolyl sulfone with sodium n-hutyl mercaptide in ethanol has been reported to give 76% of methyl p-tolyl sul- fone.' Displacement on carbon also apparently failed in a similar reaction with sodium p-tolyl mercaptide, judging from the isolation of p-tolyl disulfide as the major reaction product.' These observations and studies of the behavior of compounds like CeHjSOzCH2Cl and C1CH2SOaNa with nucleo- philes has led to the conclusion that ...