Stereochemistry of. alpha.-halo sulfoxides. II. Interdependent stereochemistry at sulfur and. alpha.-carbon in the. alpha.-halogenation of sulfoxides

P Calzavara, M Cinquini, S Colonna…

Index: Calzavara,P. et al. Journal of the American Chemical Society, 1973 , vol. 95, # 22 p. 7431 - 7436

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Citation Number: 26

Abstract

Abstract: a-Halogenation of alkyl aryl and dialkyl sulfoxides by electrophilic halogenating reagents follows two different stereochemical processes which involve either double retention or double inversion at sulfur and carbon. When the a carbon is a chiral or prochiral center, optically active sulfoxides afford only one of the two possible diastereomeric a-halo sulfoxides, whose optical purity and chirality depend on the nature of the substrate and the ...

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