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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 10
BKCSDE 30(10)
October 20, 2009 

Correlation of the Rates of Solvolysis of Methyl Fluoroformate Using the Extended Grunwald-Winstein Equation
Mi Hye Seong, Song Hee Choi, Yong Woo Lee, Jin Burm Kyong*, Dong Kook Kim, Dennis N Kevill
Methyl fluoroformate, Addition-elimination, Grunwald-Winstein equation, Solvent isotope effect
The specific rates of solvolysis of methyl fluoroformate have been measured at 40.0 oC in several hydroxylic solvents. Analysis with the extended Grunwald-Winstein equation leads to sensitivities toward changes in solvent nucleophilicity (l) of 1.33 ± 0.10 and toward changes in solvent ionizing power (m) 0.73 ± 0.06. For methanolysis, a solvent deuterium isotope effect of 3.98 is compatible with the incorporation of general-base catalysis into the substitution process. For four representative solvents, studies were made at several temperatures and activation parameters determined. These observations are also compared with those previously reported for alkyl halogenoformate esters and mechanistic conclusions are drawn.
2408 - 2412
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