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

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.

Citation

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

10.1080/10610270500419072

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

URI

http://hdl.handle.net/20.500.11937/7153

Collection

Curtin Research Publications