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

David M. Hodgson, Magnus Bebbington, Paul Willis

Research output: Contribution to journalArticleResearchpeer-review

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.

Original languageEnglish
Pages (from-to)3787-3798
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number21
DOIs
StatePublished - 7 Nov 2003

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Sulfhydryl Compounds
Nitrogen
deoxygenation
Kinetics
synthesis
thiols
nitrogen
kinetics

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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.",
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