title: Gold(III)-mediated contraction of benzene to cyclopentadiene: from p-benziporphyrin to gold(III) true tetraarylcarbaporphyrin.
abstract: The reaction of p-benziporphyrin, sodium tetrachloroaurate(III) dihydrate, and potassium carbonate in dichloromethane yielded gold(III) 5,10,15,20-tetraaryl-21-carbaporphyrin owing to the contraction of p-phenylene to cyclopentadiene. This molecule is the very first representative of a true 5,10,15,20-tetraaryl-21-carbaporphyrin complex where four trigonal donor atoms are involved in equatorial coordination. The contraction adds an unprecedented route to numerous organic transformations of aromatic compounds catalyzed by simple gold(III) compounds. p-Benziporphyrin provided the unique environment to alter the fundamental reactivity of the benzene unit facilitating its contraction to cyclopentadiene.
authors.affiliation: Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St. 50-383 Wrocław (Poland), Fax: (+48) 71-328-23-48.
authors.forename: Bartosz
authors.initials: B
authors.lastname: Szyszko
authors.forename: Kamil
authors.initials: K
authors.lastname: Kupietz
authors.forename: Ludmiła
authors.initials: L
authors.lastname: Szterenberg
authors.forename: Lechosław
authors.initials: L
authors.lastname: Latos-Grażyński
keywords: CC activation; cyclopentadiene; gold; porphyrinoids; ring contraction