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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Bibliographic Details
Published in:Canadian journal of chemistry 1983-07, Vol.61 (7), p.1472-1480
Main Authors: Hancock, James Reid, Hardstaff, William Rayne, Johns, Paul Alan, Langler, Richard Francis, Mantle, William Stanley
Format: Article
Language:English
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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.
ISSN:0008-4042
1480-3291
DOI:10.1139/v83-257