Synthesis of 3-Chloro-3-(trimethylsilyl)prop-2-enoic Acid Amidesand Hydrazides from 3-(Trimethylsilyl)propynoic Acid

A number of previously unknown and difficultly accessible polyfunctional β-chloro-β-(trimethyl­silyl)prop-2-enoic acid amides and hydrazides have been synthesized by amination of 3-chloro-3-(trimethyl­silyl)­prop-2-enoyl chloride with the corresponding amines, amino alcohols, 2-amino-4-methylpentanoic acid, and hydrazines. Initial 3-chloro-3-(trimethylsilyl)prop-2-enoyl chloride has been prepared by hydrohalogenation of 3-trimethylsilylpropynoic acid with thionyl chloride in DMF, followed by treatment with oxalyl chloride.