Abstract
The rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes in the presence of sulfuric acid affords 2-oxa-4-azabicyclo[3.3.1]non-3-en-6-one derivatives. 3-Aminocaran-4-one oximes, in which the amino group contains such substituents as acetyl, propionyl, chloroacetyl, 1-adamantylcarbonyl, benzoyl, 2-thienylcarbonyl, or anilinocarbonyl, undergo this reaction. N-Acyl derivatives of higher fatty (heptanoic and nonadecanoic) acids do not undergo this reaction. The reaction with D2SO4 leads to the replacement of all hydrogen atoms of the isopropyl group by deuterium. The mechanism of this rearrangement is proposed.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1837–1844, August, 2005.
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Agafontsev, A.M., Tkachev, A.V. Sulfuric acid-promoted rearrangement of 3-(N-acylamino)-substituted caran-4-one oximes. Russ Chem Bull 54, 1892–1899 (2005). https://doi.org/10.1007/s11172-006-0055-z
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DOI: https://doi.org/10.1007/s11172-006-0055-z