One-pot Selective Formylation and Claisen Rearrangement on Calixarenes
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A versatile synthon with formyl and allyl groups at the upper rim of calixarene has been synthesized in two steps. Selective formylation of 25,27-diallyloxy-26,28-dihydroxycalixarene, 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-diallylcalixarene is reported.
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 Calixarenes, Supramolecular Chemistry 18(2):91-95, http://dx.doi.org/10.1080/10610270500419072
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