American Chemical Society
ol201919p_si_001.pdf (20.66 MB)

Regioselective O-Substitution of C-Undecylresorcin[4]arene

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journal contribution
posted on 2011-09-16, 00:00 authored by Francesco Farina, Carmen Talotta, Carmine Gaeta, Placido Neri
Selectively functionalized resorcinarenes were obtained by weak-base-promoted O-alkylation of C-undecylresorcin[4]arene 1. Tetrasubstituted derivatives with C4-1,3,5,7, C2v-1,2,5,6, Cs-1,2,4,7, and Ci-1,2,4,6 pattern were obtained in workable yields by using K2CO3 as the base in acetone at reflux. The good regioselectivity with respect to the statistical distribution was explained in terms of preferential formation of H-bonded monoanions. Heptaaroylated resorcin[4]arenes were also easily obtained by reaction of 1 with aroyl chlorides in pyridine.