α-Chlorination and Carbonylolefination: Synthesis of Phenyl 1-Chloro-1-alken-1-yl Selenides (Chlorovinyl Phenyl Selenides)

P. Coutrot; C. Grison; M. Youssefi-Tabrizi

doi:10.1055/s-1987-27875

Synthesis 1987; 1987(2): 169-170
DOI: 10.1055/s-1987-27875

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α-Chlorination and Carbonylolefination: Synthesis of Phenyl 1-Chloro-1-alken-1-yl Selenides (Chlorovinyl Phenyl Selenides)

P. Coutrot^* , C. Grison, M. Youssefi-Tabrizi

^*Laboratoire de Chimie Organique II, U. A. CNRS 486, Université de Nancy I. B. P. 239, F-54506 Vandoeuvre-les-Nancy Cédex, France

Abstract

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The lithium derivatives prepared from diethyl phenylselenomethane-phosphonate with n-butyllithium at low temperature react with carbon tetrachloride to give the corresponding α-chlorinated phosphonate and trichloromethyllithium. The latter deprotonates the α-chlorinated phosphonate in situ to give a new lithio derivative which reacts with carbonyl compounds. These different steps take place in one pot and lead to chlorovinyl phenyl selenides, a novel class of selenocompounds.

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