Participation of sulphonamide nitrogen in the rearrangement of the 2-azabicyclo[2.2.2]octane skeleton: An efficient synthesis of the 6-azabicyclo[3.2.1]octan-4-one system

Andrew B. Holmes; Paul R. Raithby; John Thompson; Andrew J.G. Baxter; John Dixon

doi:10.1039/c39830001490

Participation of sulphonamide nitrogen in the rearrangement of the 2-azabicyclo[2.2.2]octane skeleton: An efficient synthesis of the 6-azabicyclo[3.2.1]octan-4-one system

Andrew B. Holmes, Paul R. Raithby, John Thompson, Andrew J.G. Baxter, John Dixon

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

Abstract

Treatment of the 2-azabicyclo[2.2.2]oct-5-ene imino Diels-Alder adduct (2) with N-bromosuccinimide in aqueous dimethoxyethane gives the rearranged bromohydrin (4a), whose structure is confirmed by X-ray crystallographic analysis, and which serves as a precursor to the 6-azabicyclo[3.2.1]octan-4-one (7).

Original language	English
Pages (from-to)	1490-1492
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	24
DOIs	https://doi.org/10.1039/c39830001490
Publication status	Published - 31 Dec 1983

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Participation of sulphonamide nitrogen in the rearrangement of the 2-azabicyclo[2.2.2]octane skeleton: An efficient synthesis of the 6-azabicyclo[3.2.1]octan-4-one system. / Holmes, Andrew B.; Raithby, Paul R.; Thompson, John et al.
In: Journal of the Chemical Society, Chemical Communications, No. 24, 31.12.1983, p. 1490-1492.

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

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abstract = "Treatment of the 2-azabicyclo[2.2.2]oct-5-ene imino Diels-Alder adduct (2) with N-bromosuccinimide in aqueous dimethoxyethane gives the rearranged bromohydrin (4a), whose structure is confirmed by X-ray crystallographic analysis, and which serves as a precursor to the 6-azabicyclo[3.2.1]octan-4-one (7).",

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AU - Baxter, Andrew J.G.

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AB - Treatment of the 2-azabicyclo[2.2.2]oct-5-ene imino Diels-Alder adduct (2) with N-bromosuccinimide in aqueous dimethoxyethane gives the rearranged bromohydrin (4a), whose structure is confirmed by X-ray crystallographic analysis, and which serves as a precursor to the 6-azabicyclo[3.2.1]octan-4-one (7).

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Participation of sulphonamide nitrogen in the rearrangement of the 2-azabicyclo[2.2.2]octane skeleton: An efficient synthesis of the 6-azabicyclo[3.2.1]octan-4-one system

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