Rearrangement of some allylic sulphinate esters to allylic sulphones. Ion-pair and sigmatropic shift mechanisms
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2149-2152
- https://doi.org/10.1039/p19870002149
Abstract
The mechanism of rearrangement of a number of allylic sulphinate esters to the corresponding allylic sulphones on heating in formamide has been investigated as a function of substrate structure. Simple systems such as crotyl and α-methylallyl sulphinate appear to follow a [2,3]-sigmatropic shift pathway, while others, particularly cyclohex-2-enyl sulphinates, show the characteristics of an ion-pair mechanism.Keywords
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