ol049826m_si_001.cif (30.15 kB)

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

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posted on 18.03.2004 by M. Rita Paleo, M. Isabel Calaza, Paula Graña, F. Javier Sardina
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.