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DOI: 10.1039/A901536A (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 1847-1852

Chemistry of cage-shaped hydrocarbons. Ring transformations on a tricyclo[5.2.1.0[hair space]4,10]decane system

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Tahsin J. Chow, Yung-Son Hon, Chung-Chi Jen, Jyh-Haur Chern and Kuan-Jiuh Lin

Abstract

A series of triquinane (tricyclo[5.2.1.0[hair space]4,10[hair space]]decane) derivatives were prepared from oxidation of pentaquinandiene 1. Ozonolysis of 1, followed by reduction, yielded three products 4, 5, and 6 with poly-hydroxy groups. The hydroxy group of 5 was transformed to an iodo group in 8 with triphenylphosphine and iodine. An attempted dehydroiodination of 8 with base upon heating produced 10 with an unexpected geometry. The structure of an isomer 11 has been solved by single-crystal X-ray diffraction analysis, in which an exo-oriented cyclopropyl group indicated that an inversion has happened at C(3). The mechanism of the reaction from 8 to 10 was depicted as going through a multi-step sequence as outlined in Scheme 3.

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