Competitive formation of spiro[5.5]undecane in preference to bicyclo[4.3.1]decane via type II carbonyl ene reaction

Srikrishna, Adusumilli ; Dinesh, Chikkana (2005) Competitive formation of spiro[5.5]undecane in preference to bicyclo[4.3.1]decane via type II carbonyl ene reaction Tetrahedron: Asymmetry, 16 (14). pp. 2393-2395. ISSN 0957-4166

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2005.06.011

Abstract

The presence of an isopropenyl group at the C-1 position of a 3-isopropenylcyclohexaneacetaldehyde failed to generate the spiro[4.5]decane and produced only bicyclo[4.3.1]decanol. However, the presence of a methallyl group at the C-1 position of 3-isopropenylcyclohexaneacetaldehyde generated exclusively the spiro[5.5]undecanols.

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