UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

Roy T. McBurney; Alexandra M. Z. Slawin; Laura A. Smart; Yanping Yu; John C. Walton

doi:10.1039/c1cc12720a

UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

Roy T. McBurney, Alexandra M. Z. Slawin, Laura A. Smart, Yanping Yu, John C. Walton

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

Abstract

Oxime carbonates were found to be excellent precursors for the clean and direct generation of iminyl radicals under UV irradiation. Suitably functionalised iminyls underwent cyclisations yielding various phenanthridines and also substituted quinolines and isoquinolines. EPR and X-ray analyses of oxime carbonates provided insight into the mechanism.

Original language	English
Pages (from-to)	7974-7976
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	28
DOIs	https://doi.org/10.1039/c1cc12720a
Publication status	Published - 2011

Keywords

O-PHENYL OXIMES
DIOXIME OXALATES
N-HETEROCYCLES
CYCLIZATIONS
DIHYDROPYRROLES
HETEROARENES
PRECURSORS
REAGENTS

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10.1039/c1cc12720a

Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis
Walton, J. C. (PI) & McBurney, R. T. (Researcher)
EPSRC
1/10/10 → 31/03/14
Project: Standard

Cite this

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title = "UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals",

abstract = "Oxime carbonates were found to be excellent precursors for the clean and direct generation of iminyl radicals under UV irradiation. Suitably functionalised iminyls underwent cyclisations yielding various phenanthridines and also substituted quinolines and isoquinolines. EPR and X-ray analyses of oxime carbonates provided insight into the mechanism.",

keywords = "O-PHENYL OXIMES, DIOXIME OXALATES, N-HETEROCYCLES, CYCLIZATIONS, DIHYDROPYRROLES, HETEROARENES, PRECURSORS, REAGENTS",

author = "McBurney, {Roy T.} and Slawin, {Alexandra M. Z.} and Smart, {Laura A.} and Yanping Yu and Walton, {John C.}",

year = "2011",

doi = "10.1039/c1cc12720a",

language = "English",

volume = "47",

pages = "7974--7976",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

AU - McBurney, Roy T.

AU - Slawin, Alexandra M. Z.

AU - Smart, Laura A.

AU - Yu, Yanping

AU - Walton, John C.

PY - 2011

Y1 - 2011

N2 - Oxime carbonates were found to be excellent precursors for the clean and direct generation of iminyl radicals under UV irradiation. Suitably functionalised iminyls underwent cyclisations yielding various phenanthridines and also substituted quinolines and isoquinolines. EPR and X-ray analyses of oxime carbonates provided insight into the mechanism.

AB - Oxime carbonates were found to be excellent precursors for the clean and direct generation of iminyl radicals under UV irradiation. Suitably functionalised iminyls underwent cyclisations yielding various phenanthridines and also substituted quinolines and isoquinolines. EPR and X-ray analyses of oxime carbonates provided insight into the mechanism.

KW - O-PHENYL OXIMES

KW - DIOXIME OXALATES

KW - N-HETEROCYCLES

KW - CYCLIZATIONS

KW - DIHYDROPYRROLES

KW - HETEROARENES

KW - PRECURSORS

KW - REAGENTS

U2 - 10.1039/c1cc12720a

DO - 10.1039/c1cc12720a

M3 - Article

SN - 1359-7345

VL - 47

SP - 7974

EP - 7976

JO - Chemical Communications

JF - Chemical Communications

IS - 28

ER -

UV promoted phenanthridine syntheses from oxime carbonate derived iminyl radicals

Abstract

Keywords

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Projects

Photocatalysis for Organic Synthesis: Photocatalysis for Organic Synthesis

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