Investigations on organo‐tin compounds. XI. The alkaline hydrolysis of organo‐tin esters and nitriles

In contra‐distinction to cyanomethyl‐ or ethoxycarbonylmethyl‐tin compounds, which by reaction with alkali undergo tin‐carbon bond cleavage, organo‐tin compounds containing an ester or cyano group in the β‐position or beyond with respect to the tin atom are readily converted into the corresponding carboxylic acid derivatives. 2‐Carboxyethyltin compounds spontaneously undergo a secondary reaction with formation of an inner salt. The preparation of several organotin‐carboxylic acids or their sodium salts (which show marked solubility in water) is reported. The stability of the tin‐carbon bond in relation to the position of the ester and cyano groups with respect to the tin atom is briefly discussed.