Abstract
At treatment with sulfuric acid in acetonitrile solution the verbenone (4,6,6-trimethylbicyclo[3,1.1]hept-3-en-2-one) suffers an opening of the four-membered ring with the rupture of the C1-C6 bond of the pinane skeleton and transforms into o-menthene derivatives, o-mentha-1,6-dien-3-one and 8-acetamido-o-menth-1-en-3-one, whose ratio depends on the reaction conditions. E-and Z-isomers of verbenone oxime under the same conditions undergo the Beckmann rearrangement leading to the formation of 5,7,7-trimethyl-3-azabicyclo[4.1.1]oct-4-en-2-one and 5,7,7-trimethyl-2-azabicyclo[4.1.1]oct-4-en-3-one, respectively.
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Original Russian Text © S.S. Koval’skaya, N.G. Kozlov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 8, pp. 1173–1178.
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Koval’skaya, S.S., Kozlov, N.G. Verbenone in the synthesis of o-menth-1-en-3-one and 5,7,7-trimethylazabicyclo[4.1.1]octane derivatives. Russ J Org Chem 42, 1151–1156 (2006). https://doi.org/10.1134/S1070428006080082
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DOI: https://doi.org/10.1134/S1070428006080082