Reaction of cis-carveol with triphenylphosphine and tetrachloromethane : a note on the mechanism of the Leereaction.

Ravindranath, B. and Srinivas, P. (1983) Reaction of cis-carveol with triphenylphosphine and tetrachloromethane : a note on the mechanism of the Leereaction. Tetrahedron, 39. pp. 3991-3994.

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Abstract

The title reaction yielded trans-carvyl chloride2 and pinol 3. The formation of pinol and the specific rotation of the carvyl chloride are affected by the presence of acid. The implications of these findings on the understanding of the course of the reaction are discussed. Use of an acid scavenger is recommended in application of the PPh&CL reagent for acid sensitive compounds. A bimolecular, concerted group transfer mechanism (Scheme 2) is suggested for the decomposition of the intermediate alkoxytriphenylphosphonium halide 7.

Item Type:	Article
Uncontrolled Keywords:	Lee reaction, Carvyl chloride, pinol
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions:	Plantation Products Spices and Flavour Technology
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	16 Mar 2018 06:30
Last Modified:	16 Mar 2018 06:30
URI:	http://ir.cftri.res.in/id/eprint/2858

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