Asymmetric induction in the Sommelet rearrangement of chiral benzyl sulfonium salts

SJ Campbell, D Darwish

Index: Campbell,S.J.; Darwish,D. Canadian Journal of Chemistry, 1976 , vol. 54, p. 193 - 201

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Citation Number: 13

Abstract

The Sommelet rearrangement of (+)-ethylmethyl-p-nitrobenzylsulfonium perchlorate,(+)-1, and (+)-ethylmethyl-p-chlorobenzylsulfonium perchlorate,(+)-2, are described. Elution of (+)- 1 through an hydroxide exchange resin generated ethylmethylsulfonium p-nitro-benzylide (+)-3 which decomposed in methanol at room temperature to ethyl 2-methyl-5-nitro-benzyl sulfide, 6, and (+)-methyl α-(2-methyl-5-nitrophenyl) ethyl sulfide,(+)-7, with 18 to 20.3% ...