Chemistry of Ethanediyl S, S-Acetals-4. Promising Way to Cis-Substituted Olefins, Stereoselectively from Carbonyl Compounds

R Caputo, C Ferreri, P Isita, L Longobardo…

Index: Caputo; Ferreri; Isita; Longobardo; Mastroianni; Palumbo Synthetic Communications, 1992 , vol. 22, # 9 p. 1345 - 1350

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Citation Number: 3

Abstract

Abstract Aldehydes and methyl ketones readily afford 5, 6-dihydro-1, 4-dithiins that can be converted by n-butyllithium into their corresponding sulfur stabilized carbanions. Coupling of the latter with alkyl halides leads to species having a cis-configurated, disubstituted double bond tied up by the sulfur-containing ring which is known to be susceptible of selective removal.