Radical induced cyclisations of some cyclic unsaturated allylic sulphones
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 313-317
- https://doi.org/10.1039/p19890000313
Abstract
The cyclisations of unsaturated allylic p-tolyl sulphones to give ring compounds with adjacent vinyl and p-tolylsulphonylmethyl substituents (Scheme 2) is shown to be a feasible process by the conversion, in satisfactory yield, of the allylic ether (5; R = Me) into the bicyclic sulphone (7), formed as a mixture of diastereoisomers (8) and (9). The prop-2-ynyl analogue can be similarly cyclised to the vinyl sulphones (14) and (15), the former predominating. These reactions are considered to occur by a radical chain mechanism involving addition–elimination of ArSO2˙ radicals.Keywords
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