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 W.P. Bebbington; Paul Willis

doi:10.1039/b306717n

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 W.P. Bebbington, Paul Willis

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

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 language	English
Pages (from-to)	3787-3798
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	21
DOIs	https://doi.org/10.1039/b306717n
State	Published - 7 Nov 2003

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Hodgson, D. M., Bebbington, M. W. P., & Willis, P. (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. Organic and Biomolecular Chemistry, 1(21), 3787-3798. https://doi.org/10.1039/b306717n

Hodgson, David M. ; Bebbington, Magnus W.P. ; Willis, Paul. / 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. In: Organic and Biomolecular Chemistry. 2003 ; Vol. 1, No. 21. pp. 3787-3798.

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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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Hodgson, DM, Bebbington, MWP & Willis, P 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', Organic and Biomolecular Chemistry, vol. 1, no. 21, pp. 3787-3798. https://doi.org/10.1039/b306717n

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. / Hodgson, David M.; Bebbington, Magnus W.P.; Willis, Paul.
In: Organic and Biomolecular Chemistry, Vol. 1, No. 21, 07.11.2003, p. 3787-3798.

Research output: Contribution to journal › Article › peer-review

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T1 - Development of two processes for the synthesis of bridged azabicyclic systems

T2 - Intermolecular radical addition-homoallylic rearrangements leading to 2-azanorborn-5-enes and neophyl-type radical rearrangements to 2-azabenzonorbornanes

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AU - Willis, Paul

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AB - 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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JO - Organic and Biomolecular Chemistry

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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

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