Sulphur–oxygen cleavage in the reaction of four- and five-membered sultones with hydroxide: evidence for a stereoelectronic effect in sulphonyl reactions
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 415-417
- https://doi.org/10.1039/c39880000415
Abstract
Hydroxide ion cleaves the simple 4- and 5-ring sultones (1a) and (1b) chiefly by S–O rather than the C–O bond breakage normally found with unhindered sulphonic esters; we infer that electron donation to the sulphonyl group by an attached donor atom X is a function of the C–S–X–C dihedral angle such that the electron delocalization is least with the smallest dihedral angle.Keywords
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