Photo-assisted kinetic resolution of diastereomeric limonene and carvomenthene oxides in methanol in the presence of Lewis acids

Bettadaiah, B. K. and Srinivas, P. (2004) Photo-assisted kinetic resolution of diastereomeric limonene and carvomenthene oxides in methanol in the presence of Lewis acids. Journal of Photochemistry and Photobiology A: Chemistry, 167. pp. 137-140.

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Abstract

Photosolvolysis of diastereomeric R-(+)-limonene oxide and R-(+) carvomenthene oxides in methanol, in the presence of Lewis acid catalysts viz. ZnCl2, ZnBr2 and InCl3 affords resolution of (+)-trans-limonene oxide and (+)-trans-carvomenthene oxide in excellent yield. Also, the photosolvolyzed products (1S, 2S, 4R) trans-1-methoxy-2-hydroxy-p-menthane and (1S, 2S, 4R)-trans-1-methoxy-2-hydroxy-pmenth-8-ene, could be obtained in good purity. The key factor determining the selectivity in solvolysis is the presence of isopropenyl or isopropyl group on the C-4 of limonene or carvomenthene oxides.

Item Type:	Article
Uncontrolled Keywords:	Photosolvolysis; Kinetic resolution; cis-/trans-Limonene oxide; cis-/trans-Carvomenthene oxide; Zinc halides; Lewis acid
Subjects:	600 Technology > 09 Industrial oils, fats, waxes, gases > 03 Essential oils
Divisions:	Plantation Products Spices and Flavour Technology
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	04 Jul 2007 06:28
Last Modified:	21 Jun 2012 06:40
URI:	http://ir.cftri.res.in/id/eprint/1282

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