
%0 Journal Article
%A Cameron, Donald W. 
%A Gable, Robert W. 
%A Heisey, Ross M. 
%A White, Jonathan M. 
%T Conformation of 1-Oxy Cyclohexenes Deriving from Diels-Alder Cycloaddition: Spectroscopic and X-Ray Crystal Structure Analysis
%J Australian Journal of Chemistry
%D 2000/06/26
%V 53
%N 3
%P 167-170
%K X-Ray crystallography; cycloaddition; Diels&#8211;Alder; conformation.
%R https://doi.org/10.1071/CH00036
%U https://www.publish.csiro.au/paper/CH00036 
%X For cycloadduct (6), derived by reaction of the (Z)-oxy diene (7) with the dienophile (8), the newly formed cyclohexene ring is shown by spectroscopic and X-ray crystal structure analysis to be based on the half-chair conformation (9). This contrasts with analogous diastereomeric adducts from (E)-oxy dienes, which are based on the ring-flipped conformation (4). The determinant for this conformational difference is suggested to be the stereoelectronic preference of the allylic oxy substituent, in (4) and (9), for a pseudoaxial orientation to the double bond of the cyclohexene system. 
