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Catalysts 2013, 3(3), 588-598; doi:10.3390/catal3030588

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

* ,
Molecular Design Laboratory, Biological Chemistry Research Institute, Universidad Michoacana de San Nicolás de Hidalgo, Edificio B-1, Ciudad Universitaria, Morelia, Michoacán CP 58033, Mexico
* Author to whom correspondence should be addressed.
Received: 21 April 2013 / Revised: 3 June 2013 / Accepted: 1 July 2013 / Published: 8 July 2013
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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(NO3)3-5H2O. 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 HNO3, which is released from the Bi salt.
Keywords: calixpyrrole; calix[5]pyrrole; bismuth nitrate; anion-guest calixpyrrole; calix[5]pyrrole; bismuth nitrate; anion-guest
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chacón-García, L.; Contreras-Celedón, C.A.; Tapia-Juárez, M. Isotopic Labeling Study of the Formation of Calix[5]pyrroles Catalyzed by Bi(NO3)3. Catalysts 2013, 3, 588-598.

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