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, Università di Modena e Reggio Emilia, via Campi 183, 41100 Modena, Email: prati.fabiounimore.it

A. Spaggiari, D. Vaccari, P. Davoli, G. Torre, F. Prati, J. Org. Chem., 2007, 72, 2216-2219.

DOI: 10.1021/jo061346g

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Abstract

Application of (PhO)₃P-halogen-based reagents allowed the preparation of vinyl halides 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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Key Words

Bromination, Elimination, 1,1-Dibromoalkanes

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ID: J42-Y2007-0930