title: Stanna-Brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies.
abstract: [reaction: see text] The reaction of R(3)SnLi with carboxylic acid derivatives proceeds through a novel, very fast stanna-Brook rearrangement that generates alpha-alkoxyorganolithium compounds as intermediates. The outcome of these reactions depends on the nature of the carboxyl derivatives. Reaction of R(3)SnLi 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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
authors.forename: M Rita
authors.initials: MR
authors.lastname: Paleo
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Calaza
authors.forename: Paula
authors.initials: P
authors.lastname: Graña
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Sardina