A simple and unambiguous route to adamantene: debromination of 1,2-dibromoadamantane with bis(trimethylsilyl)mercury
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 783-784
- https://doi.org/10.1039/c39790000783
Abstract
In a process extensible, in principle, to the preparation of other anti-Bredt alkenes, reaction in boiling benzene of 1,2-dibromo- or 1,2-di-iodo-adamantane with bis(trimethylsilyl)mercury, which dehalogenates 1,2-dibromoalkanes in a concerted, ‘four-centre’ manner, leads to the unambiguous generation of adamantene, as shown by trapping by 1,3-diphenylisobenzofuran (30–35% yield of adduct) and 2,5-dimethylfuran (16% yield of adduct).Keywords
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