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

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

Access to Document

Fingerprint Dive into the research topics of 'Azatriquinanes: Synthesis, Structure, and Reactivity'. Together they form a unique fingerprint.

Cite this

Hext, N. M., Hansen, J., Blake, A. J., Hibbs, D. E., Hursthouse, M. B., Shishkin, O. V., & Mascal, M. (1998). Azatriquinanes: Synthesis, Structure, and Reactivity. Journal of Organic Chemistry, 63(17), 6016-6020.

@article{5fbc8e5dbf354e25bbdf26f60f39b81a,

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",

number = "17",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=0001529798&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001529798&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0001529798

VL - 63

SP - 6016

EP - 6020

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -