NUCLEOPHILIC REACTIONS BETWEEN CYCLIC 1,2-SULFITES AND CHLORIDE-IONS

Authors
NYMANN K JENSEN L SVENDSEN JS
Citation
K. Nymann et al., NUCLEOPHILIC REACTIONS BETWEEN CYCLIC 1,2-SULFITES AND CHLORIDE-IONS, Acta chemica Scandinavica, 50(9), 1996, pp. 832-841
Citations number
26
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
50
Issue
9
Year of publication
1996
Pages
832 - 841
Database
ISI
SICI code
0904-213X(1996)50:9<832:NRBC1A>2.0.ZU;2-U
Abstract
When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohy drins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochem ical outcome of the reactions. The results showed that reversible inve rsion pathways (S(N)2 reactions) and a retention pathway (S(N)2i react ion) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.