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Catalysts  2013 

Isotopic Labeling Study of the Formation of Calix[5]pyrroles Catalyzed by Bi(NO3)3

DOI: 10.3390/catal3030588

Keywords: calixpyrrole, calix[5]pyrrole, bismuth nitrate, anion-guest

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Abstract:

One of the more elusive classes of macrocycles includes the calix[5]pyrroles, which can be obtained from pyrrole and acetone in the presence of low concentrations of Bi(NO 3) 3-5H 2O. An isotopic labeling experiment aided the proposal of a mechanism to explain the formation of calix[5]pyrrole at low acid concentrations and the exclusive formation of calix[4]pyrrole at high acid concentrations. We assume that the mechanism involves HNO 3, which is released from the Bi salt.

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