Gold(III)‐Mediated Contraction of Benzene to Cyclopentadiene: From p‐Benziporphyrin to Gold(III) True Tetraarylcarbaporphyrin |
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| Authors: | Bartosz Szyszko Kamil Kupietz Dr. Ludmiła Szterenberg Prof. Lechosław Latos‐Grażyński |
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| Affiliation: | Department of Chemistry, University of Wroc?aw, 14 F. Joliot‐Curie St. 50‐383 Wroc?aw (Poland), Fax: (+48)?71‐328‐23‐48 |
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| 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. |
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| Keywords: | C C activation cyclopentadiene gold porphyrinoids ring contraction |
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