Construction of n-bridged molecular ribbons and cavities

This thesis presents the most comprehensive approach to the synthesis of structures containing fused 7-azanorbornanes yet described. In particular, many of the high pressure reactions involving the cycloaddition of pyrroles and isoindoles to ring-strained alkenes, especially those involving norbornenes, are new and extremely versatile. Methods have been developed to control the stereoselectivity of these cycloadditions and many new molecular architectures such as I, II have been produced.

The other major contribution discovered in this area has been the preparation of a new type of atropisomer. This has involved preparation of the diazanorbomadiene VII and its screening by etheno bridges. For the first time, two stable atropisomers (e.g. VIII and IX) have been able to be isolated.

The structural work in this thesis has involved substantial X-ray structure analysis (17 structures) as well as advance NMR methodology. The work on the dynamic of N -Z rotation in bridged alicycles has given land -breaking results.