Sulfur-Stabilized Carbanions: Electrophilic Reactions of an Allylic Anion Containing Propanedithio and Phenylthio Substituents
Resource
Synlett 1990: 285-286
Journal
Synlett
Date Issued
1990
Author(s)
Chen, Ming-Yi
Abstract
In contrast to the γ-regioselective reactions of 1,1,3-tris(phenylthio)propene, the anion of 2-(2-phenylthioethylidene)-1,3-dithiane reacts with halides and aldehydes preferentially at the propanedithio-substituted carbon (α-regioselective reaction), but at the phenylthio-substituted carbon with open-chain aliphatic ketones.This umpolung reagent is utilized to prepare α,β-unsaturated ketones and oxygen-containing heterocyclic compounds.
SDGs
Type
journal article