X-ray structural analysis of ester and ether derivatives of 4,5-endo,endo-9,10-dimethanonaphthalene-11-ol: Evidence for πσ CO*Participation in the Ground State

Abstract

Application of the variable oxygen probe to the polycyclic alcohol 11 and its crystalline ester and ether derivatives provides evidence for a weak interaction between the neighbouring homo-allylic -system and the COR bond; there is no evidence for interaction with the remote -system. Analysis of the carboncarbon bond distances in 1114 reveals structural effects consistent with the manifestation of one of the two possible retro-DielsAlder reactions in the ground state. © CSIRO 2008.