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Gold(III)‐Mediated Contraction of Benzene to Cyclopentadiene: From p ‐Benziporphyrin to Gold(III) True Tetraarylcarbaporphyrin
Author(s) -
Szyszko Bartosz,
Kupietz Kamil,
Szterenberg Ludmiła,
LatosGrażyński Lechosław
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304162
Subject(s) - cyclopentadiene , chemistry , dichloromethane , contraction (grammar) , benzene , potassium , medicinal chemistry , inorganic chemistry , organic chemistry , catalysis , medicine , solvent
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.