Issue 21, 2003

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

Abstract

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
12 Jun 2003
Accepted
04 Aug 2003
First published
22 Aug 2003

Org. Biomol. Chem., 2003,1, 3787-3798

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

D. M. Hodgson, M. W. P. Bebbington and P. Willis, Org. Biomol. Chem., 2003, 1, 3787 DOI: 10.1039/B306717N

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