A Mild Synthesis of Vinyl Halides and gem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents

Alberto Spaggiari, Daniele Vaccari, Paolo Davoli, Giovanni Torre, and Fabio Prati*
Dipartimento di Chimica, Universit di Modena e Reggio Emilia, via Campi 183, 41100 Modena, Italy prati.fabio@unimore.it
J. Org. Chem., 2007, 72 (6), pp 2216–2219
DOI: 10.1021/jo061346g
Publication Date (Web): February 13, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A new application of (PhO)3P−halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.

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History

  • Published In Issue March 16, 2007
  • Received June 29, 2006

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