title: Thermolysis of 1-(1-aryl-1-bromomethyl)cyclopropyl bromides: a reinvestigation.
abstract: Two compounds, the (Z)- and (E)-isomers of 2,4-dibromo-1-p-tolyl-1-butene 2a and 3a, respectively, were isolated in 65% total yield when 1-(1-bromo-1-p-tolylmethyl)cyclopropyl bromide (1a) was heated at 150 degrees C for 1 h. 1,1-Dibromo-2-p-tolylcyclobutane (4a), previously reported to be the only product in this reaction, was not detected. The phenyl analogue of 1a reacted similarly and gave the (Z)- and (E)-isomers of 2,4-dibromo-1-phenyl-1-butene 2b and 3b, respectively, in 60% yield. A rationale for the reaction is presented.
authors.affiliation: Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria.
authors.forename: Tore
authors.initials: T
authors.lastname: Nordvik
authors.forename: Udo H
authors.initials: UH
authors.lastname: Brinker