Abstract
Under the conditions of the Polonovsky reaction, N-(2,7-dimethyl-2,7-octadienyl)-N,N-dimethylamine oxide gives 2,7-dimethyl-2,7-octadienal and N-(2,7-dimethyl-2,7-octadienyl)-N-methylacetamide. Under the same conditions, N-(2,7-dimethyl-2,7-octadienyl)-N,N-dietnylamine oxide dihydrate does not undergo the Polonovsky reaction and gives the rearrangement product, O-(1-isopropenyl-5-methyl-5-hexenyl)-N,N-diethylhydroxylamine, and the hydration product, O-[1-(1-hydroxy-1-methyl)ethyi-5-methyl-5-hexenyl]-N,N-diethylhydroxylamine.
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The work was accomplished under the financial support of the Russian Fund for the Fundamental Research (93-03-4219).
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1588–1590, September, 1993.
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Petrushkina, E.A., Galakhov, M.V. & Zakharkin, L.L. Reaction of acetic anhydride with monoterpene amine oxides possessing the 2,7-dimethyloctane skeleton. Russ Chem Bull 42, 1522–1524 (1993). https://doi.org/10.1007/BF00699187
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DOI: https://doi.org/10.1007/BF00699187