title: Attempted generation of the potentially aromatic 6,7-diphenyldibenzo[e,g][1,4]diazocine dianion leads with profound rearrangement to the isomeric n-(2-amino-1,2-diphenylethenyl)carbazole dianions.
abstract: The attempted generation of the potentially aromatic 6,7-diphenyldibenzo[e,g][1,4]diazocine dianion from sodium in THF leads with profound rearrangement to the isomeric N-(2-amino-1,2-diphenylethenyl)carbazole dianions and, after hydrolysis, to a 55:45 mixture of Z- and E-isomers of N-(2-amino-1,2-diphenylethenyl)carbazoles. These isomers were separated and their individual structures determined by X-ray diffraction. Since treatment of the starting diazocine first with tert-butyllithium and then with water also yielded the same Z- and E-isomeric mixture, electron transfer reduction is clearly involved.
authors.affiliation: Department of Chemistry, State University of New York at Binghamton, Binghamton, New York 13902-6000, USA. jjeisch@binghamton.edu
authors.forename: John J
authors.initials: JJ
authors.lastname: Eisch
authors.forename: Renuka N
authors.initials: RN
authors.lastname: Manchanayakage
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold