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Gold(III)-mediated Contraction of Benzene to Cyclopentadiene: From P-Benziporphyrin to gold(III) True Tetraarylcarbaporphyrin

Gold(III)-mediated Contraction of Benzene to Cyclopentadiene: From P-Benziporphyrin to gold(III) True Tetraarylcarbaporphyrin

Bartosz Szyszko, Kamil Kupietz, Ludmiła Szterenberg, Lechosław Latos-Grażyński

Chemistry. 2014 Jan 27;20(5):1376-82.

PMID: 24382653

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13874027	Sodium tetrachloroaurate(III) dihydrate		13874-02-7	Price

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