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

M. Mocerino, M.I. Ogden, J.K. Pettersen, Brian Skelton, Allan White

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)91-95
JournalSupramolecular Chemistry
Volume18
Issue number2
DOIs
Publication statusPublished - 2006

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