Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1,2-Benzisoxazole, is researched, Molecular C7H5NO, CAS is 271-95-4, about Chemical evolution. XVII. Mechanisms of the photochemical rearrangements of ortho-substituted benzene derivatives and related heterocycles.Name: 1,2-Benzisoxazole.
The mechanisms of the photochem. rearrangements of isoxazoles, 2-cyanophenol, pyrazoles, and anthranilonitriles were investigated by using low-temperature techniques. Isonitrile (I) was detected by ir (2130 cm-1) and uv in the photoconversion of indoxazene to benzoxazole. I was further identified by independent synthesis and hydrolysis to the formanilide in acid. 2-Cyanophenol (II) is also formed on photolysis of indoxazene; however, no intermediate could be detected in this conversion. Quenching and sensitization studies suggest that the formation of benzoxazole proceeds from the singlet and II from the triplet excited states. The solvent dependence of the reaction suggests that benzoxazole is formed from an initial π,π* excitation and II is formed from an n,π* excitation. The photoconversion of II to benzoxazole may also proceed by I as shown by the uv spectrum of the reaction mixture after irradiation at – 77°. No intermediates were identified in the photochem. conversion of indazoles to benzimidazoles and anthranilonitriles using the above techniques. Emission measurements of the singlet and triplet energies of all the compounds used in this study are reported.
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