title: Azulene-Naphthalene-Type Rearrangements in Benz[a]azulene and Cyclohepta[b]indole.
abstract: Flash vacuum pyrolysis (FVP) of benz[a]azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclohepta[b]indole similarly yields phenanthridine and 2-cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2-ethynylbiphenyl and 2-isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene-vinylidene mechanism of the azulene-naphthalene rearrangement, whereas other proposed mechanisms are ruled out.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia. wentrup@uq.edu.au.
authors.forename: Curt
authors.initials: C
authors.lastname: Wentrup
authors.affiliation: Fachbereich Chemie der Philipps-Universität, D-35037, Marburg, Germany.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Becker
keywords: arenes; flash vacuum pyrolysis; hetarenes; reaction mechanisms; rearrangement