Abstract
Abstract Cyclohexanone oxime hydrogen sulfate was found to undergo facile rearrangement to 3,4,5,6-tetrahydro-2H-azepin-7-ol hydrogen sulfate in the presence of ε-caprolactam–tin tetrachloride complex, while the oxime hydrogen sulfate decomposed in the presence of ε-caprolactam. Other metal halides were studied to see if the oxime hydrogen sulfate undergoes rearrangement in the presence of the lactam. Gyclohexanone oxime–tin tetrachloride complex was synthesized. Its reaction with the tetrahydroazepin-7-ol hydrogen sulfate was found to give the lactam–tin tetrachloride complex and the oxime hydrogen sulfate which regenerated the tetrahydro-azepin-7-ol hydrogen sulfate in the reaction system. Tin tetrachloride complex was prepared with several oximes.
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