150919-07-6Relevant articles and documents
Tetra-O-benzylated Calixarenes with C4 Symmetry
Neri, Placido,Geraci, Corrada,Piattelli, Mario
, p. 3319 - 3322 (1993)
The first procedure for the selective partial O-alkylation of p-tert-butylcalixarene 1 affording well defined products is described.Treatment of 1 with p-X-benzyl bromides (X = H, Me, tert-Bu, NO2, CN) and K2CO3 in THF/DMF gives the corresponding 1,3,5,7-tetrabenzyl ethers 2-6 having C4 symmetry.Their structures were firmly established by FAB(+) MS, 1H- and 13C-NMR.Variable temperature NMR studies evidenced conformational flexibility for 2-6.A possible rationale is proposed in order to explain the origin of the 1,3,5,7-substitution pattern. Key words: calixarenes, tetraalkylation, 1,3,5,7-tetrabenzyl ethers, C4 symmetry.