REACTIVITY OF SUBSTITUTED PHENYLDIMETHYLSULFONIUM IONS WITH COMMON NUCLEOPHILES - A TEST OF PK(1G)(ME) FOR PHENYLDIMETHYLSULFONIUM SALTS AND A COMPARISON WITH METHYL ARENESULFONATES

Authors
FOUNTAIN KR DUNKIN TW PATEL KD
Citation
Kr. Fountain et al., REACTIVITY OF SUBSTITUTED PHENYLDIMETHYLSULFONIUM IONS WITH COMMON NUCLEOPHILES - A TEST OF PK(1G)(ME) FOR PHENYLDIMETHYLSULFONIUM SALTS AND A COMPARISON WITH METHYL ARENESULFONATES, Journal of organic chemistry, 62(11), 1997, pp. 3711-3714
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
11
Year of publication
1997
Pages
3711 - 3714
Database
ISI
SICI code
0022-3263(1997)62:11<3711:ROSPIW>2.0.ZU;2-C
Abstract
The correlations of nucleophilic rate data for phenyldimethylsulfonium ions with common nucleophiles with pK(lg)(Me) values shows that the s lopes of the line, beta(lg)(Me), correlate qualitatively with Edwards hardness parameter for the nucleophile, and not with the Swain-Scott n (o) parameter. Comparison with substituted methyl arenesulfonates show s different leaving group behavior in the two systems. These results s upport Shaik's hypothesis that leaving group behavior consists of some SET character.