Unexpected single-step formation of 1,2-anti-heterodisubstituted calix[4]arenes upon alkylation of a tribenzoyl precursor.
The selective preparation and complete structural characterization of a small series of 1,2-anti-heterodisubstituted calix[4]arenes has been accomplished. These compounds were obtained in two steps from unsubstituted p-tert-butylcalix[4]arene by tribenzoylation and a subsequent one-pot, two-step sequence involving alkylation with simultaneous partial deacylation, resulting in heterodisubstituted calixarenes carrying an alkyl and an aroyl group. The monoalkyl-tribenzoyl intermediate, prior to in situ deprotection, could also be isolated.
Universidad Autónoma de Madrid, Departamento de Química Orgánica, C-I, Cantoblanco, 28049-Madrid, Spain. kleij@science.uva.nl
Arjan W
AW
Kleij
Beatriz
B
Souto
César J
CJ
Pastor
Pilar
P
Prados
Javier
J
de Mendoza