NEW ASPECTS OF NITROSATION OF ARYLCYCLOPROPANES: NITROSATION OF PHENYLCYCLOPROPANES WITH BULKY ALKYL SUBSTITUENTS IN THE SMALL RING

Authors

  • О. Б. Бондаренко M. V. Lomonosov Moscow State University, Moscow 119991
  • А. Ю. Гаврилова M. V. Lomonosov Moscow State University, Moscow 119991
  • Л. Г. Сагинова M. V. Lomonosov Moscow State University, Moscow 119991
  • Н. В. Зык M. V. Lomonosov Moscow State University, Moscow 119991
  • Н. С. Зефиров M. V. Lomonosov Moscow State University, Moscow 119991

DOI:

https://doi.org/10.1007/7224

Keywords:

1-alkyl-2-phenylcyclopropanes, isoxazolines, 1, 2-oxazines, ∆1-pyrroline N-oxide, nitrosation, skeletal rearrangement

Abstract

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 ∆1-pyrroline N-oxide are formed, formation of the latter is preceded by skeletal rearrangement.

How to Cite
Bondarenko, O. B.; Gavrilova, A. Yu.; Saginova, L. G.; Zyk, N. V.;  Zefirov, N. S.  Chem. Heterocycl. Compd. 2008, 44, 1275. [Khim. Geterotsikl. Soedin. 2008, 1566.]

For this article in the English edition see DOI 10.1007/s10593-009-0184-z


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Published

2022-11-29

Issue

No. 10 (2008)

Section

Original Papers