Regiochemistry and reactivity in the chlorination of sulfides
Huheey's original method for the calculation of substituent electronegativities is modified so that isomeric groups have different electronegativities. The modified form of Huheey's method is then employed to show that our previously published method for anticipating regiochemistry in asym...
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Published in | Canadian journal of chemistry Vol. 61; no. 7; pp. 1472 - 1480 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Ottawa, Canada
NRC Research Press
01.07.1983
|
Online Access | Get full text |
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Summary: | Huheey's original method for the calculation of substituent electronegativities is modified so that isomeric groups have different electronegativities. The modified form of Huheey's method is then employed to show that our previously published method for anticipating regiochemistry in asymmetric sulfide chlorinations, i.e., ΔX
P
calculations for the α and α′ substituents in the sulfide substrates, is successful in all fifty known cases. A new reactivity function (R
P
) is defined, for the sulfenium ion intermediates, which permits one to anticipate when substrates become inert to chlorine in exhaustive chlorinations conducted in aprotic media. |
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ISSN: | 0008-4042 1480-3291 |
DOI: | 10.1139/v83-257 |