POPELLANES-LII THE REACTION OF CONJUGATED DIENIC PROPELLANES WITH SINGLET OXYGEN

Article abstract of DOI:10.1016/S0040-4020(01)97726-9

The reactions of propellanes containing one or two cyclohexadiene rings with singlet oxygen take the course of exclusive syn-attack with respect to a hetero-ring containing two CO groups.When only one or no CO group is found in the hetero ring, both syn- and anti-attack occur.The former course is interpreted in terms of secondary orbital interactions wich stabilize the transition state for syn-attack.