It has been shown for the first time that nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring proceeds predominantly with attack of the nitrosonium cation on the benzyl carbon atom of the cyclopropane ring with intermediate formation of an alkyl carbocation. In addition to isoxazolines, 1,2-oxazines and Δ1-pyrroline N-oxide are formed, formation of the latter is preceded by skeletal rearrangement.
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Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1566-1575, October, 2008.
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Bondarenko, O.B., Gavrilova, A.Y., Saginova, L.G. et al. New aspects of nitrosation of arylcyclopropanes: nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring. Chem Heterocycl Comp 44, 1275–1283 (2008). https://doi.org/10.1007/s10593-009-0184-z
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DOI: https://doi.org/10.1007/s10593-009-0184-z