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Paper | Regular issue | Vol 34, No. 8, 1992, pp.1583-1604
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6073
1,3-Cycloaddition of Benzonitrile Oxides to Diazepines. I. 1-Ethoxycarbonyl-5-methyl-1,2-diazepine

Paolo Beltrame,* Enzo Cadoni, Maria M. Carnasciali, Gioanna Gelli, Adolfo Lai, Angelo Mugnoli, and Marcella Pani

*Dipartimento di Chimica Fisica ed Elettrochimica, Università, Via Golgi 19, I-20133 Milano, Italy


Stable aryl nitrile oxides (1a-e) and 1-ethoxycarbonyl-5-methyl-1,2-diazepine (2) undergo 1,3-cycloaddition reactions to give isomeric 1,2,4-oxadiazole (3), 4,5-dihydroisoxazole (4) and isoxazole (5) derivatives, the first one being in any case the most abundant product. Overall kinetics were measured at temperatures in the range 50-90 °C, in 1,1,2,2-tetrachloroethane and mixtures of the latter with DMF; rate coefficients for the parallel reactions were, thus, obtained. Substituent and solvent effects are discussed.