A facile route to bicyclo(2.1.1)hexanes was developed involving
the intramolecular photocyclization of 1, 5-hexadien-3-one to
bicyclo(2.1.1)hexan-2-one. A study of the chemistry of bicyclo-(2.1.1)hexan-2-one was undertaken. Deuterium exchange and borohydride
reduction demonstrated the strain present in the ketone.
Further evidence was obtained from the failure to introduce substituents
alpha to the carbonyl group, a usually facile reaction and a
necessary step in desired ring contraction studies.
After numerous unsuccessful attempts to introduce a double
bond into the bicyclo(2.1.1) hexane system, a successful route to
the parent bicyclo(2.1.1) hexene was achieved. The key step involved
dehydrohalogenation of 2-bromobicyclo(2.1.1)hexane. Some preliminary
studies of the olefin have been carried out and its thermolysis
studied
