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.
1,3-cycloaddition of benzonitrile oxides to diazepines . I. 1-ethoxycarbonyl-5-methyl-1,2-diazepine
CARNASCIALI, MARIA;PANI, MARCELLA
1992-01-01
Abstract
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.
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