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RESEARCH ARTICLE
Contents Vol 66(10)

1,2-Disilabicyclo[1.1.1]pentan-4-ones from a Disilenide and Acryloyl Chlorides

Andreas Rammo A , Iulia Bejan A , Antje Meltzer A , Krzysztof Radacki B , Holger Braunschweig B and David Scheschkewitz A C
+ Author Affiliations
- Author Affiliations

A Saarland University, Krupp-Chair for General and Inorganic Chemistry, Campus Dudweiler, Am Markt, Zeile 1, 66125 Saarbrücken-Dudweiler, Germany.

B Julius-Maximilian-University, Institute of Inorganic Chemistry, Am Hubland, 97074 Würzburg, Germany.

C Corresponding author. Email: scheschkewitz@mx.uni-saarland.de

Australian Journal of Chemistry 66(10) 1311-1314 https://doi.org/10.1071/CH13265
Submitted: 23 May 2013  Accepted: 19 June 2013   Published: 25 July 2013

Abstract

Reactions of a disilenide, a disila analogue of vinyl lithiums, with two α,β-unsaturated carboxylic acid chlorides yield the first examples of compounds with a bicyclo[1.1.1]pentane scaffold that feature one carbon and one silicon atom at bridgehead positions; the formation of 1,2-disilabicyclo[1.1.1]pentan-4-ones is explained with initial nucleophilic substitution at the carbonyl C-atom by the nucleophilic disilenide and subsequent intramolecular [2+2]-cycloaddition of the Si=Si to the C=C double bond in a highly diastereoselective fashion.


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