Title

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

Document Type

Article

Publication Date

11-7-2003

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.

DOI

10.1039/b306717n

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