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Photochemical Transformation of Terpenes and their Derivatives

Jafarkhan, K.T. (2006) Photochemical Transformation of Terpenes and their Derivatives. [Student Project Report]

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Abstract

This Dissertation / Report is the outcome of investigation carried out by the creator(s) / author(s) at the department/division of Central Food Technological Research Institute (CFTRI), Mysore mentioned below in this page.

Item Type: Student Project Report
Additional Information: Epoxides are important intermediates in the functionalization of olefins to oxygenated compounds. Oxirane ring undergoes a variety of ring opening and rearrangement reactions in the presence of various acid and base catalysts. While these aspects of chemistry of epoxides are well studied, their photochemical transformations are relatively less explored. Present work describes the results of photo irradiation reactions of styrene oxide and terpinolene oxide in the presence of various Lewis acid catalysts and in aprotic solvents like benzene, at different temperatures and wavelengths of irradiation. The photoreaction of styrene oxide afforded bromohydrin and bibenzyl with the relative ratios of these products, the rate and the course of the reaction depending on the wavelength of the irradiation and the temperature of the reaction. Based on the results, a pathway to the formation of these products has been envisaged. The photo irradiation of terpinolene oxide in presence of indium chloride in aprotic solvents has been studied in detail. Rearrangement of terpinolene oxide, a spiro epoxide, to a cyclic ether, 8,9-dehydro-1,4- cineol is being reported for the first time. As 8,9-dhehydro-1,4-cineol is readily reduced to 1,4-cineol, the present reaction constitutes to a facile synthesis of 1,4-cineol.
Uncontrolled Keywords: Terpenes Photochemical Transformation
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 33 Terpenoids Chemistry
600 Technology > 08 Food technology > 06 Preservation and Storage > 04 Irradiation
Divisions: Plantation Products Spices and Flavour Technology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 12 Apr 2007
Last Modified: 28 Dec 2011 09:26
URI: http://ir.cftri.com/id/eprint/456

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