Spirodienone and Bis(spirodienone) Derivatives of Calixnaphthalenes
journal contributionposted on 20.02.1998, 00:00 by Paris E. Georghiou, Muhammad Ashram, Howard J. Clase, John N. Bridson
Calixnaphthalenes 11 and 12 in which hydroxyl groups are situated intraannularly can be oxidized with PTMATB and base to form the bis(spirodienone) 13, from 11, and bis(spirodienone) 20−21 and spirodienone 22, from 12. The prototype calixnaphthalenes 9 and 10 previously reported by us and which contain similar 1,5 dihydroxy functionalities extrannularly failed to afford the analogous spironaphthalenones. Model studies with the bis(1-hydroxy-2-naphthyl)methanes 8−8f provided support for the putative mechanism proposed for the formation of spirodienone calixarenes and spironaphthalenones. The synthesis of the novel tert-butylcalixnaphthalenes 12 is described.