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Studies in sesquiterpenes-XIX. Action of perbenzoic acid on longifolene

Nayak, Ramdas U and Dev, Sukh (1963) Studies in sesquiterpenes-XIX. Action of perbenzoic acid on longifolene. In: Tetrahedron, 19 (12). pp. 2269-2280.

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Official URL: http://dx.doi.org/10.1016/0040-4020(63)85043-7


Oxidation of longifolene, a mono-olefinic sesquiterpene, with a chloroform solution of perbenzoic acid proceeded to almost two mole consumption of the peracid to furnish a number of products, important ones being an α-ketol, a norketone (longicamphenilone) and the corresponding C14-alcohols. Under certain conditions it has been possible to arrest the reaction at one mole consumption and to isolate longifolene-α-epoxide, which is the major product; some amounts of epimeric longifolaldehydes and longicamphenilone were also formed. Further action of perbenzoic acid on longifolene oxide and longifolaldehydes has been investigated and the results used to interpret the mechanism of abnormal peracid oxidation of longifolene.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 22 Jun 2010 08:57
Last Modified: 19 Sep 2010 06:07
URI: http://eprints.iisc.ac.in/id/eprint/28132

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