In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 66, No. 11 ( 1988-11-01), p. 2870-2879
Abstract:
Substitution reactions adjacent to sulfonyl groups are known to proceed with difficulty, and there is evidence to suggest that these may not necessarily proceed by an S N 2 pathway. The mechanism of these reactions could be studied in principle by using the conversion of α-chloro-β-hydroxysulfones of known configuration into α,β-epoxysulfones of known configuration. This paper describes results in which this has been attempted. However, the stereochemical aspects of the epoxide formation could not be assigned unequivocally because of the intervention of a very facile "retro-aldol" process when the chlorohydrins are subjected to treatment with bases, although the experimental results do suggest that the reaction does proceed in a regular S N 2-like manner, with inversion at carbon. The X-ray crystal structures of two highly substituted α,β-epoxysulfones are presented, thus putting the structures, including stereochemistry, of a range of these compounds on firm ground.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
1988
detail.hit.zdb_id:
1482256-8
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