Chemoselective reaction of a sulfonate ester with methoxide ions in preference to benzyl mercaptide anions

RF Langler, NA Morrison

Index: Langler, Richard Francis; Morrison, Nancy Ann Canadian Journal of Chemistry, 1987 , vol. 65, p. 2385 - 2389

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Citation Number: 10

Abstract

Trifluoroethyl benzyl sulfide was prepared (in 2-propanol) and subsequently chlorinated as a further test of substituent electronegativity based regiochemical predictions. The initial attempt to prepare that sulfide by reaction of 2, 2, 2-trifluoroethyl methanesulfonate and benzyl mercaptide anions (in methanol) furnished benzyl methyl sulfide. Mechanistic possibilities are discussed in detail and some synthetic consequences of this novel ...