Photochemistry of Benzotriazole: An Unprecedented Tautomer-Selective Intermolecular [2+2] Photocycloaddition

Kevin I. Booker-Milburn; Paul M. Wood; Richard F. Dainty; Michael W. Urquhart; Andrew J. White; Helen J. Lyon; Jonathan P H Charmant

doi:10.1021/ol025693y

Photochemistry of Benzotriazole: An Unprecedented Tautomer-Selective Intermolecular [2+2] Photocycloaddition

Kevin I. Booker-Milburn^*, Paul M. Wood, Richard F. Dainty, Michael W. Urquhart, Andrew J. White, Helen J. Lyon, Jonathan P H Charmant

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

28 Citations (Scopus)

Abstract

(matrix presented) Irradiation of benzotriazole with a variety of maleimide derivatives leads to the stereo- and regioselective formation of aryl [2 + 2] photocycloaddition products. Further studies with 2-alkyl benzotriazole derivatives indicates that in the case of the parent benzotriazole this cycloaddition proceeds selectively via the 2H-tautomer.

Original language	English
Pages (from-to)	1487-1489
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	9
DOIs	https://doi.org/10.1021/ol025693y
Publication status	Published - 2 May 2002

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Publisher: Am. Chem. Soc

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title = "Photochemistry of Benzotriazole: An Unprecedented Tautomer-Selective Intermolecular [2+2] Photocycloaddition",

abstract = "(matrix presented) Irradiation of benzotriazole with a variety of maleimide derivatives leads to the stereo- and regioselective formation of aryl [2 + 2] photocycloaddition products. Further studies with 2-alkyl benzotriazole derivatives indicates that in the case of the parent benzotriazole this cycloaddition proceeds selectively via the 2H-tautomer.",

author = "Booker-Milburn, {Kevin I.} and Wood, {Paul M.} and Dainty, {Richard F.} and Urquhart, {Michael W.} and White, {Andrew J.} and Lyon, {Helen J.} and Charmant, {Jonathan P H}",

note = "Publisher: Am. Chem. Soc",

year = "2002",

month = may,

day = "2",

doi = "10.1021/ol025693y",

language = "English",

volume = "4",

pages = "1487--1489",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Photochemistry of Benzotriazole

T2 - An Unprecedented Tautomer-Selective Intermolecular [2+2] Photocycloaddition

AU - Booker-Milburn, Kevin I.

AU - Wood, Paul M.

AU - Dainty, Richard F.

AU - Urquhart, Michael W.

AU - White, Andrew J.

AU - Lyon, Helen J.

AU - Charmant, Jonathan P H

N1 - Publisher: Am. Chem. Soc

PY - 2002/5/2

Y1 - 2002/5/2

N2 - (matrix presented) Irradiation of benzotriazole with a variety of maleimide derivatives leads to the stereo- and regioselective formation of aryl [2 + 2] photocycloaddition products. Further studies with 2-alkyl benzotriazole derivatives indicates that in the case of the parent benzotriazole this cycloaddition proceeds selectively via the 2H-tautomer.

AB - (matrix presented) Irradiation of benzotriazole with a variety of maleimide derivatives leads to the stereo- and regioselective formation of aryl [2 + 2] photocycloaddition products. Further studies with 2-alkyl benzotriazole derivatives indicates that in the case of the parent benzotriazole this cycloaddition proceeds selectively via the 2H-tautomer.

UR - http://www.scopus.com/inward/record.url?scp=0041761650&partnerID=8YFLogxK

U2 - 10.1021/ol025693y

DO - 10.1021/ol025693y

M3 - Article (Academic Journal)

C2 - 11975610

VL - 4

SP - 1487

EP - 1489

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 9

ER -

Photochemistry of Benzotriazole: An Unprecedented Tautomer-Selective Intermolecular [2+2] Photocycloaddition

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