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Trends in Organic Chemistry   Volumes    Volume 19 
Classical tosylate/chloride leaving group approach supports a tetrahedral transition state for additions to trigonal carbon
Malcolm J. D’Souza, Jeremy Wirick, Jasbir Deol, Dennis N. Kevill
Pages: 1 - 11
Number of pages: 11
Trends in Organic Chemistry
Volume 19 

Copyright © 2018 Research Trends. All rights reserved

The experimentally measured rates of solvolysis of 2-chloroethoxycarbonyl chloride (2-chloroethyl chloroformate, 3), 2-chloroethoxycarbonyl p-toluenesufonate (5), and phenoxycarbonyl p-toluenesulfonate (6) were followed at 25.0 °C in various pure and binary aqueous-organic solvents with varying degrees of polarity. An analysis of the rate constants for 3, 5, and 6, was carried out using the two-term extended Grunwald-Winstein equation and comparisons are made to the previously published results for ethyl and phenyl chloroformate esters. The kOTS/kCl rate ratios and the Grunwald-Winstein l/m ratios indicate the probability of a dominant bimolecular carbonyl-addition pathway in the more nucleophilic solvents. Nevertheless in 3 and 5, in the strongly hydrogen-bonding 70% and 50% HFIP mixtures, a side-by-side ionization mechanism is favored.    
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