TY - JOUR
T1 - One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes
AU - Mocerino, M.
AU - Ogden, M.I.
AU - Pettersen, J.K.
AU - Skelton, Brian
AU - White, Allan
PY - 2006
Y1 - 2006
N2 - 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.
AB - 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.
U2 - 10.1080/10610270500419072
DO - 10.1080/10610270500419072
M3 - Article
SN - 1061-0278
VL - 18
SP - 91
EP - 95
JO - Supramolecular Chemistry
JF - Supramolecular Chemistry
IS - 2
ER -