Issue 26, 2012
From the journal:

Organic & Biomolecular Chemistry

Highly efficient intramolecular Cannizzaro reaction between 1,3-distal formyl groups at the upper rim of a cone-calix[4]arene†

Marzia Galli,a   José Augusto Berrocal,a   Stefano Di Stefano,*a   Roberta Cacciapaglia,a   Luigi Mandolini,a   Laura Baldini,b   Alessandro Casnatib  and  Franco Ugozzolic  

* Corresponding authors

a Dipartimento di Chimica and IMC/CNR, Università La Sapienza, P.le A. Moro 5, 00185 Rome, Italy
E-mail: stefano.distefano@uniroma1.it

b Dipartimento di Chimica Organica ed Industriale, Università di Parma, Parco Area delle Scienze 17/A, I-43124, Parma, Italy

c Dipartimento di Chimica Analitica e Chimica Fisica, Università di Parma, Parco Area delle Scienze 17/A, I-43124, Parma, Italy

Abstract

The 1,3-distal cone-calix[4]arene dialdehyde 1 undergoes Cannizzaro disproportionation in the presence of strong base, but its 1,2-vicinal regioisomer 3 and the analogous monoaldehyde 2 are unreactive under the same conditions. The high intramolecular reactivity of the 1,3-distal regioisomer 1 is measured and discussed in terms of Effective Molarity (EM).

Graphical abstract: Highly efficient intramolecular Cannizzaro reaction between 1,3-distal formyl groups at the upper rim of a cone-calix[4]arene

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Article information

DOI
https://doi.org/10.1039/C2OB25458A
Article type
Paper
Submitted
01 Mar 2012
Accepted
03 May 2012
First published
03 May 2012

Org. Biomol. Chem., 2012,10, 5109-5112

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Highly efficient intramolecular Cannizzaro reaction between 1,3-distal formyl groups at the upper rim of a cone-calix[4]arene

M. Galli, J. A. Berrocal, S. Di Stefano, R. Cacciapaglia, L. Mandolini, L. Baldini, A. Casnati and F. Ugozzoli, Org. Biomol. Chem., 2012, 10, 5109 DOI: 10.1039/C2OB25458A

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