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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 9
BKCSDE 29(9)
September 20, 2008 

Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Fluoroformate and a Consideration of Leaving Group Effects
Mi Hye Seong, Jin Burm Kyong*, Dong Kook Kim, Dennis N Kevill
n-Propyl fluoroformate, Addition-elimination, Grunwald-Winstein equation, Leaving group effect
Reactions of n-propyl fluoroformate in a variety of pure and binary solvents have been studied at 40.0 oC. The extended (two-term) Grunwald-Winstein equation has been applied to the specific rates of solvolysis of n-propyl fluoroformate. The sensitivities (l = 1.80 ± 0.17 and m = 0.96 ± 0.10) to changes in solvent nucleophilicity and solvent ionizing power and the kF/kCl values are similar to those for solvolyses of n-octyl fluoroformate over the full range of solvents, suggesting that the addition step of an addition-elimination mechanism is ratedetermining. These observations are also compared with those previously reported for the corresponding chloroformate and fluoroformate esters.
1747 - 1751
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