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Report | Regular issue | Vol 16, No. 8, 1981, pp.1345-1351
Published online, 1st January, 1970
DOI: 10.3987/R-1981-08-1345
Bicyclic Peroxides from a 1,4-Diazepine

V. T. Ramakrishnan and Joseph H. Boyer*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor St., Chicago, IL 60607-7061, U.S.A.

Abstract

An adduct, 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]non-3-ene, was obtained from 2,3-dicyano-5,7-dimethyl-6H-1,4-diazepine and hydrogen peroxide in the presence of alkali or a tertiary amine. It was dehydrogenated by iodobenzene diacetate into 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo[4.2.1]nona-2,4-diene; further oxidation by m-chloroperbenzoic acid gave 4,5-dicyano-1,8-dimethyl-2,7-diaza-3,6,9,10-tetraoxatetracyclo[6.2.1.02,405,7]undecane.