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Synlett 1997; 1997(5): 595-596
DOI: 10.1055/s-1997-3227
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Stereoconservative Formation and Reactivity of α-Chalcogen-Functionalized Vinyllithium Compounds from α-Bromo-vinylic Chalcogenides

Antonio L. Braga* , Gilson Zeni, Leandro H. de Andrade, Claudio C. Silveira
  • *Laboratório de Preparação e Aplicações Sintéticas de Organocalcogênio, Departamento di Química, Universidade Federal de Santa Maria, 97.119-900, Santa Maria, RS, Brasil
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Publication Date:
31 December 2000 (online)

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Bromine/lithium exchange was performed upon treatment of α-bromo-vinylic chalcogenides with butyllithium in hexane at room temperature to provide α-chalcogen-vinyllithium intermediates quantitatively. Addition of electrophiles to the lithiated compounds gave the corresponding functionalized vinylic chalcogenides in good yields with retention of configuration.

vinylic bromide - vinylic chalcogenides - Br/Li exchange reaction