A Kinetic Study of the Solvolyses of Methyl and Ethyl Chloroglyoxalates

Solvolyses of methyl and ethyl chloroglyoxylates proceed about 106 times faster than the identical solvolyses of the corresponding chloroformates. The correlation parameters obtained from application of the extended Grunwald−Winstein equation are consistent with an addition−elimination (association−...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-10, Vol.70 (22), p.9032-9035
Main Authors: Kevill, Dennis N, Park, Byoung-Chun, Kyong, Jin Burm
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Solutions
Solvation. Solvent properties
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Summary:Solvolyses of methyl and ethyl chloroglyoxylates proceed about 106 times faster than the identical solvolyses of the corresponding chloroformates. The correlation parameters obtained from application of the extended Grunwald−Winstein equation are consistent with an addition−elimination (association−dissociation) mechanism over the full range of solvents, with the addition step being rate determining.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050998m