Synthesis 2006(21): 3739-3745  
DOI: 10.1055/s-2006-950238
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Highly Stereoselective Approach toward (Z)-1,2-Bis(silyl)ethenes

Piotr Pawluć, Bogdan Marciniec*, Beata Dudziec, Grzegorz Hreczycho, Maciej Kubicki
Department of Organometallic Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland
Fax: +48(61)8291508; e-Mail: marcinb@amu.edu.pl;
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Publikationsverlauf

Received 10 May 2006
Publikationsdatum:
09. Oktober 2006 (online)

Abstract

A new flexible and stereoselective protocol for the synthesis of the compounds of the general formula, (Z)-Ph2RSiCH=CHSiRPh2 (where R is an alkyl, alkenyl or alkoxy substituent) has been developed. The title compounds have been efficiently obtained by ruthenium hydride complex [RuHCl(CO)(PCy3)2]-catalyzed (Z)-selective silylative coupling cyclization of 1,2-bis(diphenylvinylsiloxy)ethane or N,N′-dimethyl-N,N′-di(diphenylvinylsilyl)ethane-1,2-diamine to generate respective disilacyclic platforms, followed by their reaction with Grignard reagents or alcohols. (Z)-Bis(silyl)ethenes could not be synthesized by a metathesis procedure.

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Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-292109. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336 033;
e-mail: deposit@ccdc.cam.ac.uk).