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

Authors :
Rammo, Andreas
Bejan, Iulia
Meltzer, Antje
Radacki, Krzysztof
Braunschweig, Holger
Scheschkewitz, David
Source :
Australian Journal of Chemistry. 2013, Vol. 66 Issue 10, p1311-1314. 8p.
Publication Year :
2013

Abstract

Reactions of a disilenide, a disila analogue of vinyl lithiums, with two &#945,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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00049425
Volume :
66
Issue :
10
Database :
Academic Search Index
Journal :
Australian Journal of Chemistry
Publication Type :
Academic Journal
Accession number :
92801499
Full Text :
https://doi.org/10.1071/CH13265