CYCLOADDITION REACTION OF BENZOCYCLOPROPENE WITH AROMATIC NITRILE OXIDES: A SYNTHETIC ENTRY INTO A BRIDGED OXAZONINE
- 5 December 1979
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 8 (12) , 1431-1434
- https://doi.org/10.1246/cl.1979.1431
Abstract
9-Aryl-7-oxa-8-azatricyclo[4.3.1.0]deca-2,4,8-trienes (Ia and Ib) were synthesized by the cycloaddition reaction of benzocyclopropene with benzonitrile oxide and mesitonitrile oxide, respectively. The closed norcaradiene structures were preferable to the opened bridged oxazonine isomers in the range of 25–120°C.Keywords
This publication has 12 references indexed in Scilit:
- Effect of substituents in controlling the rate of the intramolecular cycloaddition reaction of allyl-substituted 2H-azirinesThe Journal of Organic Chemistry, 1978
- Synthesis and chemistry of benzocyclopropenesAccounts of Chemical Research, 1978
- Zur Imidazolbildung aus 2H‐Azirinen bzw. Vinylaziden und Nitrilen unter SäurekatalyseHelvetica Chimica Acta, 1978
- Photochemical transformations of small ring heterocyclic compounds. 82. Intramolecular dipolar cycloaddition reactions of unsaturated 2H-azirinesJournal of the American Chemical Society, 1977
- Synthesis and study of select heterocyclesPublished by Walter de Gruyter GmbH ,1975
- BenzocyclopropenesChemical Reviews, 1973
- Studies on heterocyclic chemistry—VTetrahedron, 1970
- 1,5-Methanocyclononatetraenyl AnionJournal of the American Chemical Society, 1966
- Nitrile Oxides. V. Stable Aromatic Nitrile Oxides1,2The Journal of Organic Chemistry, 1965
- 1.3‐Dipolare Cycloadditionen Rückschau und AusblickAngewandte Chemie, 1963