title: Regioselective O-substitution of C-undecylresorcin[4]arene.
abstract: Selectively functionalized resorcinarenes were obtained by weak-base-promoted O-alkylation of C-undecylresorcin[4]arene 1. Tetrasubstituted derivatives with C(4)-1,3,5,7, C(2v)-1,2,5,6, C(s)-1,2,4,7, and C(i)-1,2,4,6 pattern were obtained in workable yields by using K(2)CO(3) 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.
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno, Via Ponte don Melillo, I-84084 Fisciano, Salerno, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Farina
authors.forename: Carmen
authors.initials: C
authors.lastname: Talotta
authors.forename: Carmine
authors.initials: C
authors.lastname: Gaeta
authors.forename: Placido
authors.initials: P
authors.lastname: Neri
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine