Preliminary communication

Reactivity of Some Tertiary Chlorides with Methoxy and Olefinic Neighboring Group

Stanko Borčić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, P. 0. Box 156, 10000 Zagreb, Croatia
Olga Kronja ; Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, P. 0. Box 156, 10000 Zagreb, Croatia
Krešimir Humski ; Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, P. 0. Box 156, 10000 Zagreb, Croatia
Sandra Miletić ; Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, P. 0. Box 156, 10000 Zagreb, Croatia

Abstract

Solvolysis rates of tertiary chlorides 1-6 and their hexadeuterated analogs 1-dg-6-đe were measured in ethanol (q> = 80%) and 2,2,2- trifluoroethanol (w = 97%). The (5-deuterium KIE calculated showed that chloride 1 solvolyzes with n-participation of the methoxy group in the rate determining step, while chloride 2 solvolyzes mainly by way of a kc process. Based on the reduced P-deuterium isotope effect, it was also concluded that in the solvolysis of chloride 5 7t-electrons take part in the rate-determining step.

Keywords

Hrčak ID:

136672

URI

https://hrcak.srce.hr/136672

Publication date:

3.6.1996.

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