Development of two processes for the synthesis of bridged azabicyclic systems: intermolecular radical addition-homoallylic rearrangements leading to 2-azanorborn-5-enes and neophyl-type radical rearrangements to 2-azabenzonorbornanes.
Radical thiol additions to 7-azanorbornadienes give 7-thio-substituted 2-azanorbornenes and Barton deoxygenations of 7-azabenzonorbornanols give 2-azabenzonorbornanes. The processes both involve novel nitrogen-directed radical rearrangements. The kinetics and mechanisms of the reactions are also discussed.
Hodgson
David M
DM
Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK OX1 3QY. david.hodgson@chem.ox.ac.uk
Bebbington
Magnus W P
MW
Willis
Paul
P