Stanna-Brook Rearrangement of Carboxylic Acid Derivatives. Synthetic Utility and Mechanistic Studies

The reaction of R3SnLi with carboxylic acid derivatives proceeds through a novel, very fast stanna-Brook rearrangement that generates
α-alkoxyorganolithium compounds as intermediates. The outcome of these reactions depends on the nature of the carboxyl derivatives.
Reaction of R3SnLi with ester derivatives gives rise to coupled products through a novel C−C bond formation reaction. Experimental evidence
of the detailed reaction mechanism is provided.