The Thermal and Photolytic Rearrangements of Isatoic Acid Diazide

Abstract

The primary objective of this research has been the thermolysis and photolysis of isatoic acid diazide 1. Thermolysis in low boiling solvents produced the acylazido benzimidazolone 10, while refluxing in high boiling solvents gave rise to the imidazoindazoline 31, presumably via Curtius rearrangements. Photolysis of the diazide in methylene chloride gave rise to two photo products, 10 and 31, while photolysis in tetrahydrofuran produced only 31. A study of the spectral and chemical characteristics of these products have been carried out

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