Reaction of Organotin Hydrides with Acid Chlorides. Mechanism of Aldehyde and Ester Formation

Article abstract of DOI:10.1021/ja00322a031

Tri-n-butyltin hydride reacts with acid chloride, RCOCl, spontaneously at ambient temperatures to form n-Bu3SnCl, RCHO, RC(O)OCH2R, and a number of minor products.The reaction is not a radical chain process, nor are radicals involved as intermediates.The initial products are n-Bu3SnCl and RCHO; it is not known whether these are formed in a direct reaction between n-Bu3SnH and RCOCl or via an unstable chloroalkyloxytin species, n-Bu3SnOCHClR.The remaining products are formed by subsequent reactions of the aldehyde.Thus, the alkoxytin species, n-Bu3SnOCH2R, is formed from aldehyde and tin hydride.This can react further with RCH2Cl to form the ester RC(O)OCH2R, with RCOCl to form n-Bu3SnOCH(R)OCH2R, and with n-Bu3SnH to form RCH2OH.The aldehyde can also react with RCOCl to form the α'-chloro ester, RC(O)OCHClR.