Stereoselective Synthesis of
Alkynyl Vinyl Chalcogenides via Horner-Wittig Reaction

Claudio C. Silveira; Francieli Rinaldi; Rafael C. Guadagnin; Antonio L. Braga

doi:10.1055/s-0028-1083322

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Synthesis 2009(3): 469-473
DOI: 10.1055/s-0028-1083322

PAPER

Stereoselective Synthesis of Alkynyl Vinyl Chalcogenides via Horner-Wittig Reaction

Claudio C. Silveira*, Francieli Rinaldi, Rafael C. Guadagnin, Antonio L. Braga
Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Fax: +55(55)32208754; e-Mail: silveira@quimica.ufsm.br;

Further Information

Publication History

Received 4 September 2008
Publication Date:
09 January 2009 (online)

Abstract
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Abstract

New (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides were prepared by the reaction of (diphenylphosphoryl)methyl p-toluenesulfonate with alkynethiols, -selenols, or -tellurols at room temperature. The (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides reacted with aldehydes and cyclic ketones to give the corresponding alkynyl vinyl sulfides, selenides, or tellurides, with preferential E-stereochemistry, in a Horner-Wittig-type reaction.

Key words

Wittig reaction - alkynyl vinyl chalcogenides - vinyl chalcogenides - chalcogenium - olefination

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