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Int. J. Mol. Sci. 2006, 7(7), 186-196; doi:10.3390/i7070186
Article

Rate and Product Studies of Solvolyses of Benzyl Fluoroformate

1,* , 1 and 2,*
1 Department of Chemistry and Applied Chemistry, Hanyang University, Ansan-si, Gyeonggi-do 426-791, Korea. 2 Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, U.S.A.
* Authors to whom correspondence should be addressed.
Received: 19 March 2006 / Accepted: 21 June 2006 / Published: 5 July 2006
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Abstract

The specific rates of solvolysis of benzyl fluoroformate have been measured inseveral hydroxylic solvents at 25.0 °C. For methanolysis, the solvent deuterium isotopeeffect and activation parameters were determined and activation parameters were alsodetermined for solvolyses in ethanol and 80% ethanol. For several of the binary hydroxylicsolvents, measurement of product ratios allowed selectivity values to be determined. Anextended Grunwald–Winstein treatment of the data led to sensitivities to changes in solventnucleophilicity and ionizing power. Comparison with previously determined specific ratesfor solvolysis of the chloroformate gave fluorine/chlorine rate ratios greater than unity. Allof the determinations made were consistent with an addition–elimination (association–dissociation) mechanism, with addition rate-determining.
Keywords: benzyl fluoroformate; addition–elimination; solvent isotope effect; Grunwald– Winstein equation; product selectivity. benzyl fluoroformate; addition–elimination; solvent isotope effect; Grunwald– Winstein equation; product selectivity.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kyong, J.B.; Ryu, S.H.; Kevill, D.N. Rate and Product Studies of Solvolyses of Benzyl Fluoroformate. Int. J. Mol. Sci. 2006, 7, 186-196.

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