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Synthesis 2002(10): 1347-1350
DOI: 10.1055/s-2002-33123
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of (E)-α-Selenenylvinylsilanes via the Hydromagnesiation Reaction of Alkynylsilanes

Hong Zhao, Mingzhong Cai*
Department of Chemistry, Jiangxi Normal University, Nanchang 330027, P. R. China
Fax: +86(791)8511619; e-Mail: Caimz@fm365.com;
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Publication History

Received 5 March 2002
Publication Date:
01 August 2002 (online)

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Abstract

(E)-α-Selenenylvinylsilanes have been synthesized stereoselectively via the hydromagnesiation of alkynylsilanes, followed by the reaction with arylselenenyl bromides. (E)-α-Selenenylvinylsilanes can undergo the desilylation reaction in the presence of a catalytic amount of hydriodic acid to give (E)-vinyl selenides in high yields.

Key words

hydromagnesiation - (E)-α-selenenylvinylsilane - alkynylsilane - stereoselectivity - (E)-vinyl selenide