Die Umlagerung der Addukte von Säuren an Push-Pull-Acetylene : Ihre Anwendung in der Peptid-Synthese

Abstract

Push-pull-acetylenes (1) react rapidly and smoothly with proton acids to yield 3-dialkylamino-3-X-acrylic derivatives, which rearrange under very mild conditions (and in the case of the adducts of carboxylic acids quantitatively) to 3-X-N,N-dialkyl-acrylamides. After a literature survey of earlier findings concerning this rearrangement, the synthesis of push-pull-acetylenes and the course of addition of proton acids to the acetylenes is summarised. The main part deals with the preparative applications and the mechanistic aspects of the rearrangement. This reaction plays an important role in peptide synthesis by means of push-pull-acetylenes.