Medium-ring 1,5-dienes. Part II. The radical and electrophile-induced cyclisation of germacra-1(10),4,7(11)-triene
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 22,p. 2326-2332
- https://doi.org/10.1039/p19750002326
Abstract
The (E,E)-cyclodeca-1,5-diene derivative, germacra-1(10),4,7(11)-triene (1), has been cyclised to a variety of trans-decalin (selinane) derivatives by using the electrophilic reagents hypobromous acid, mercury(II) acetate, and sulphuric acid and radical-mediated reactions with benzenethiol, diphenyl disulphide, and carbon tetrachloride. A concerted mechanism in combination with a preferred reacting conformation is proposed to account for the high regio- and stereo-specificity of the reactions.Keywords
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