Azatriquinanes: Synthesis, Structure, and Reactivity

Nicholas M. Hext; Jens Hansen; Alexander J. Blake; David E. Hibbs; Michael B. Hursthouse; Oleg V. Shishkin; Mark Mascal

Azatriquinanes: Synthesis, Structure, and Reactivity

Nicholas M. Hext, Jens Hansen, Alexander J. Blake, David E. Hibbs, Michael B. Hursthouse, Oleg V. Shishkin, Mark Mascal

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

Abstract

Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

Original language	English (US)
Pages (from-to)	6016-6020
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	63
Issue number	17
State	Published - Aug 21 1998
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Azatriquinanes: Synthesis, Structure, and Reactivity",

abstract = "Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.",

author = "Hext, {Nicholas M.} and Jens Hansen and Blake, {Alexander J.} and Hibbs, {David E.} and Hursthouse, {Michael B.} and Shishkin, {Oleg V.} and Mark Mascal",

year = "1998",

month = aug,

day = "21",

language = "English (US)",

volume = "63",

pages = "6016--6020",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Azatriquinanes

T2 - Synthesis, Structure, and Reactivity

AU - Hext, Nicholas M.

AU - Hansen, Jens

AU - Blake, Alexander J.

AU - Hibbs, David E.

AU - Hursthouse, Michael B.

AU - Shishkin, Oleg V.

AU - Mascal, Mark

PY - 1998/8/21

Y1 - 1998/8/21

N2 - Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

AB - Azatriquinane, a tricyclic amine with rigid, hemispherical topology, is synthesized in six steps from pyrrole. This first example of a [2.2.2]cyclazine can be oxidatively dimerized to a novel, highly strained heptacycle or oxidized with chlorine to give an azatriquinacene, a theoretical precursor to diazadodecahedrane via Woodward dimerization.

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M3 - Article

AN - SCOPUS:0001529798

VL - 63

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EP - 6020

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

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ER -

Azatriquinanes: Synthesis, Structure, and Reactivity

Abstract

ASJC Scopus subject areas

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