1. 1,2-Disilabicyclo[1.1.1]pentan-4-ones from a Disilenide and Acryloyl Chlorides.
- Author
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Rammo, Andreas, Bejan, Iulia, Meltzer, Antje, Radacki, Krzysztof, Braunschweig, Holger, and Scheschkewitz, David
- Subjects
- *
CARBOXYLIC acids , *CHLORIDES , *NUCLEOPHILIC substitution reactions , *RING formation (Chemistry) , *CRYSTALLIZATION - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2013
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