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Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

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Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones. / Clarke, Aimee K.; Unsworth, William P.; Taylor, Richard J.K.

In: Tetrahedron, 03.02.2018.

Research output: Contribution to journalArticle

Harvard

Clarke, AK, Unsworth, WP & Taylor, RJK 2018, 'Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones', Tetrahedron. https://doi.org/10.1016/j.tet.2018.02.003

APA

Clarke, A. K., Unsworth, W. P., & Taylor, R. J. K. (2018). Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones. Tetrahedron. https://doi.org/10.1016/j.tet.2018.02.003

Vancouver

Clarke AK, Unsworth WP, Taylor RJK. Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones. Tetrahedron. 2018 Feb 3. https://doi.org/10.1016/j.tet.2018.02.003

Author

Clarke, Aimee K. ; Unsworth, William P. ; Taylor, Richard J.K. / Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones. In: Tetrahedron. 2018.

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@article{4ef63e3acd7b448f9b88251bdad36fac,
title = "Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones",
abstract = "The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.",
keywords = "Anisole, Buchner reaction, Divergent reactivity, Phenol, α-Diazocarbonyl compounds",
author = "Clarke, {Aimee K.} and Unsworth, {William P.} and Taylor, {Richard J.K.}",
note = "{\circledC} Elsevier, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.",
year = "2018",
month = "2",
day = "3",
doi = "10.1016/j.tet.2018.02.003",
language = "English",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",

}

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TY - JOUR

T1 - Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

AU - Clarke, Aimee K.

AU - Unsworth, William P.

AU - Taylor, Richard J.K.

N1 - © Elsevier, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

PY - 2018/2/3

Y1 - 2018/2/3

N2 - The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

AB - The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

KW - Anisole

KW - Buchner reaction

KW - Divergent reactivity

KW - Phenol

KW - α-Diazocarbonyl compounds

UR - http://www.scopus.com/inward/record.url?scp=85044386619&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.02.003

DO - 10.1016/j.tet.2018.02.003

M3 - Article

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -