BENZYL-4,5-DIHYDROISOXAZOLES FROM BENZYLCYCLO- PROPANES: REGIOSELECTIVE INSERTION OF AN N=O FRAGMENT INTO THE THREE-MEMBERED CARBOCYCLE OF BENZYLCYCLOPROPANES BY THE ACTION OF NITROUS ACID

Authors

  • Р. А. Газзаева K. L. Khetagurov North-Ossetian State University
  • Е. В. Трофимова M. V. Lomonosov Moscow State University
  • А. З. Каджаева K. L. Khetagurov North-Ossetian State University
  • А. Н. Федотов M. V. Lomonosov Moscow State University
  • С. С. Мочалов M. V. Lomonosov Moscow State University

DOI:

https://doi.org/10.1007/1016

Keywords:

benzylcyclopropanes, benzyl-4, 5-dihydroisoxazoles, nitrous acid, heterocyclization induced by the nitrosyl cation, nitrosylation, SET mechanism

Abstract

The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system.

Authors: R. A. Gazzaeva, E. V. Trofimova, A. Z. Kadzhaeva,
A. N. Fedotov, and S. S. Mochalov

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (8), pp 1220-1227

http://link.springer.com/article/10.1007/s10593-012-1125-9

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Published

2013-10-17

Issue

No. 8 (2012)

Section

Original Papers