Canadian Journal of Chemistry

Neighboring Group Participation in the Halogenation of Sulfoxides

T Durst, KC Tin, MJV Marcil

Index: Durst,T. et al. Canadian Journal of Chemistry, 1973 , vol. 51, p. 1704 - 1712

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Citation Number: 29

Abstract

PhS (O)(CH2) n CH2OH (n= 1-3) react with sulfuryl chloride at-78° or 0° in methylene chloride to give the corresponding PhSO2 (CH2) n CH2Cl. Evidence is presented that cyclic alkoxyoxosulfonium salts are intermediates in these transformations. When n= 4 only chlorination α to the sulfoxide function was observed. The sulfinyl carboxylic acids PhS (O)(CH2) n CO2H (n= 1-3) and amides PhS (O)(CH2) n CONH2 (n= 1-3) were also ...