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

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 (i...

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Bibliographic Details
Published in:Canadian journal of chemistry 1987-10, Vol.65 (10), p.2385-2389
Main Authors: Langler, Richard Francis, Morrison, Nancy Ann
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary: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 reaction are presented.
ISSN:0008-4042
1480-3291
DOI:10.1139/v87-398