Saline Hydrides and Superbases. 14. Rapid Elimination Reactions of Vinyl Ethers and Sulfides with Potassium 3-Aminopropylamide. Vinyl Sulfides as Acetylene Equivalents

Abstract

Potassium 3-aminopropylamide reacts rapidly with vinyl sulfides and vinyl ethers at room temperature to produce elimination products; vinyl sulfides yield alkynes with a high degree of selectivity, while vinyl ethers yield dienes or mixtures of dienes and alkynes. The reaction allows a mild, efficient transformation of vinyl sulfides into terminal acetylenes. © 1978, American Chemical Society. All rights reserved.