A highly pyramidalized cage alkene formed via the double Diels-Alder cycloaddition of syn-4,5,13,14-bis(dehydro)octafluoroparacyclophane to anthracene.
[reaction: see text] A double Diels-Alder reaction of the formal syn-bis(dehydro)octafluoroparacyclophane with anthracene leads to formation of a novel cage compound that contains a highly pyramidal double bond. The measures of pyramidality of this double bond constitute what appear to be the highest combined values of psi and phi (34.3 degrees and 33.5 degrees, respectively) yet reported to have been determined by X-ray crystallography. This cage compound, although stable indefinitely as a crystalline compound in air, exhibits the high reactivity with both triplet and singlet O2 in solution that is characteristic of such highly pyramidal pi systems.
Dolbier
William R
WR
Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
Zhai
Yi-An
YA
Battiste
Merle A
MA
Abboud
Khalil A
KA
Ghiviriga
Ion
I