The first examples of doubly bridged calix[7]arenes 2a-h have been obtained by by base-promoted O-alkylation of p-tert-butylcalix[7] arene 1 or 1.4-tetramethylene-bridged calix[7]arene 3a with a variety of bis-electrophiles including BrCH2Cl. oligoethylene glycol ditosylates, and 1,2-bis(bromomethyl)benzebe. In the presence of Cs2CO3 as the base, in acetone, the syn-1.4:2,3-bis-bridged regioisomer was obtained in yields up to 76%. Assignment of bridging pattern was based on chemical shift of OH groups in conjunction with chemical correlations with known compounds. Stereochemical bind conformational features were investigated with the aid of 2D and Dynamic NMR studies and MM3 calculations
Regioselective double intramolecular bridging of p-tert-butylcalix[7]arene
MARTINO, Marco;GAETA, CARMINE;NERI, Placido
2004-01-01
Abstract
The first examples of doubly bridged calix[7]arenes 2a-h have been obtained by by base-promoted O-alkylation of p-tert-butylcalix[7] arene 1 or 1.4-tetramethylene-bridged calix[7]arene 3a with a variety of bis-electrophiles including BrCH2Cl. oligoethylene glycol ditosylates, and 1,2-bis(bromomethyl)benzebe. In the presence of Cs2CO3 as the base, in acetone, the syn-1.4:2,3-bis-bridged regioisomer was obtained in yields up to 76%. Assignment of bridging pattern was based on chemical shift of OH groups in conjunction with chemical correlations with known compounds. Stereochemical bind conformational features were investigated with the aid of 2D and Dynamic NMR studies and MM3 calculationsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
