Mitsuo Masaki, Masaru Uchida, Kiyoshi Fukui
1973
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
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 e-caprolactam and the corresponding hydrogen sulfate of the reagents in good yields. Treatment with cyclohexylamine or benzylamine afforded e-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.