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Synthesis and Isomerization of Tricyclo[7.3.1.02,7]tridecen-13-ones

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Abstract

Dehydration of 2-hydroxy-8-R-tricyclo[7.3.1.02 , 7]tridecan-13-ones (R = H, Me, Ph) effected by various reagents provided 8-R-tricyclo[7.3.1.02 , 7]tridecen-13-ones with different positions of the double bond. In the presence of phosphoric acid arise isomers with the double bond in 2(3) position, a mixture of hydrochloric and acetic acid primarily affords isomers with the double bond in 2(7) position that further migrates into 7(8) position at R = Me, Ph.

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Rostovskaya, M.F., Vysotskaya, T.A., Grigorchuk, V.P. et al. Synthesis and Isomerization of Tricyclo[7.3.1.02,7]tridecen-13-ones. Russian Journal of Organic Chemistry 37, 1414–1417 (2001). https://doi.org/10.1023/A:1013423205456

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