Atropisomerism in 1,5-bridged calix[8]arenes.
[structure: see text] The first example of two discrete calix[8]arene conformational isomers, 2 and 2a, has been obtained by exhaustive benzylation of 1,5-tetramethylene-bridged calix[8]arene 1. It is demonstrated, with the aid of X-ray crystallography, that these atropisomers have two 3/4-cone halves oriented syn or anti with respect to the bridge/bridgeheads moiety. VT NMR studies indicate that the tert-butyl-through-the-annulus inversion is inhibited in 1, while groups larger than n-hexyl or benzyl are required for curtailing the O-through-the-annulus route.
Consoli
Grazia M L
GM
Istituto di Chimica Biomolecolare - Sezione di Catania, CNR, Via del Santuario 110, I-95028 Valverde (CT), Italy.
Cunsolo
Francesca
F
Geraci
Corrada
C
Gavuzzo
Enrico
E
Neri
Placido
P