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Abstract
Abstract The reaction of 3,4,5,6-tetrahydro-2H-azepin-7-ol hydrogen sulfate with nucleophilic reagents was studied. The tetrahydroazepin-7-ol hydrogen sulfate reacted with alcohols and oximes to give respectively ε-caprolactam and the corresponding hydrogen sulfate of the reagents in good yields. Treatment with cyclohexylamine or benzylamine afforded ε-caprolactam, the amine salt of the corresponding sulfamic acid, and the corresponding amine salt of the tetrahydroazepin-7-ol hydrogen sulfate, while anilinium phenylsulfamate was formed exclusively in the reaction with aniline. From these results, the tetrahydroazepin-7-ol hydrogen sulfate was confirmed to undergo exclusively a cleavage of the oxygen-sulfur bond by an attack of nucleophiles on the sulfur atom.
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