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One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes

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Authors
Mocerino, Mauro
Ogden, Mark
Pettersen, Jade
Skelton, B.
White, A.
Date
2006
Type
Journal Article

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Mocerino, Mauro and Ogden, Mark and Pettersen, Jade and Skelton, Brian and White, Allan. 2006. One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes. Supramolecular Chemistry 18 (2): 91-95.
Source Title
Supramolecular Chemistry
DOI
Faculty
Department of Applied Chemistry
Division of Engineering, Science and Computing
Faculty of Science
Remarks

This is an electronic version of an article published in Mocerino, Mauro and Ogden, Mark and Pettersen, Jade and Skelton, Brian and White, Allan (2006) One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes, Supramolecular Chemistry 18(2):91-95, http://dx.doi.org/10.1080/10610270500419072

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Abstract

A versatile synthon with formyl and allyl groups at the upper rim of calix[4]arene has been synthesized in two steps. Selective formylation of 25,27-diallyloxy-26,28-dihydroxycalix[4]arene, along with the Claisen rearrangement of the allyl groups, was achieved by reaction with hexamethylenetetraamine (hexamine) in glacial acetic acid. A control reaction of the dipropyl analogue shows that the selective formylation takes place independently of the Claisen rearrangement. The crystal structure of the dimethylacetal derivative of 5,17-diformyl-11,23-diallylcalix[4]arene is reported.