Studies in group IV organometallic chemistry. XVIII: The reaction of trialkyltin hydrides with alkyl propiolates†

The reaction of trialkyltin hydrides with alkyl propiolates results in the formation of at least six products. The structure of five compounds has been established by gas chromatography, infrared and nuclear magnetic resonance spectroscopy, and elementary analysis. The main products are shown to be α-trialkylstannyl- and cis- and trans-β-trialkylstannyl-acrylates. With decreasing size of the substituents on tin nonterminal addition of the trialkylstannyl group, resulting in the formation of α-trialkylstannylacrylate, becomes the predominant reaction.