Selective substitution of corroles: Nitration, hydroformylation, and chlorosulfonation

Irena Saltsman, Atif Mahammed, Israel Goldberg, Elena Tkachenko, Mark Botoshansky, Zeev Gross

Research output: Contribution to journalArticlepeer-review

Abstract

This work demonstrates the feasibility and powerfulness of electrophilic substitution on the peripheral carbon atoms of triarylcorroles as a synthetic tool to new derivatives. The large difference in the reactivity of the various carbon atoms on the macrocycle was shown to be of electronic rather than steric origin. A careful choice of reagents and a delicate control of reaction conditions allowed the selective syntheses of novel derivatives, in all of which substitution took place selectively in only the directly joined pyrrole rings of the macrocycle. This was proven by a combination of X-ray crystallography of the various products and detailed analysis of their NMR spectra.

Original languageEnglish
Pages (from-to)7411-7420
Number of pages10
JournalJournal of the American Chemical Society
Volume124
Issue number25
DOIs
StatePublished - 26 Jun 2002

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