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
DOI:
https://doi.org/10.1007/1016Keywords:
benzylcyclopropanes, benzyl-4, 5-dihydroisoxazoles, nitrous acid, heterocyclization induced by the nitrosyl cation, nitrosylation, SET mechanismAbstract
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