Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition: A dual approach using tunable UV lasers and time-dependent DFT

David M E Davies; Craig Murray; Malcolm Berry; Andrew J. Orr-Ewing; Kevin I. Booker-Milburn

doi:10.1021/jo062316g

Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition: A dual approach using tunable UV lasers and time-dependent DFT

David M E Davies, Craig Murray, Malcolm Berry, Andrew J. Orr-Ewing^*, Kevin I. Booker-Milburn

^*Corresponding author for this work

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

26 Citations (Scopus)

Abstract

(Chemical Equation Presented) An in-depth study of the intramolecular [5 + 2] photocycloaddition of maleimides using tunable UV lasers has demonstrated that the peak in quantum yield and rate both occur at wavelengths some 50 nm red shifted from the maxima observed in the UV spectra. A detailed explanation for these findings using time-dependent DFT calculations is presented, and the implications for a previously adopted mechanism are discussed. © 2007 American Chemical Society.

Original language	English
Pages (from-to)	1449-1457
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	72
Issue number	4
DOIs	https://doi.org/10.1021/jo062316g
Publication status	Published - 16 Feb 2007

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10.1021/jo062316g

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title = "Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition: A dual approach using tunable UV lasers and time-dependent DFT",

abstract = "(Chemical Equation Presented) An in-depth study of the intramolecular [5 + 2] photocycloaddition of maleimides using tunable UV lasers has demonstrated that the peak in quantum yield and rate both occur at wavelengths some 50 nm red shifted from the maxima observed in the UV spectra. A detailed explanation for these findings using time-dependent DFT calculations is presented, and the implications for a previously adopted mechanism are discussed. {\textcopyright} 2007 American Chemical Society.",

author = "Davies, {David M E} and Craig Murray and Malcolm Berry and Orr-Ewing, {Andrew J.} and Booker-Milburn, {Kevin I.}",

year = "2007",

month = feb,

day = "16",

doi = "10.1021/jo062316g",

language = "English",

volume = "72",

pages = "1449--1457",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition : A dual approach using tunable UV lasers and time-dependent DFT. / Davies, David M E; Murray, Craig; Berry, Malcolm; Orr-Ewing, Andrew J.; Booker-Milburn, Kevin I.

In: Journal of Organic Chemistry, Vol. 72, No. 4, 16.02.2007, p. 1449-1457.

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

TY - JOUR

T1 - Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition

T2 - A dual approach using tunable UV lasers and time-dependent DFT

AU - Davies, David M E

AU - Murray, Craig

AU - Berry, Malcolm

AU - Orr-Ewing, Andrew J.

AU - Booker-Milburn, Kevin I.

PY - 2007/2/16

Y1 - 2007/2/16

N2 - (Chemical Equation Presented) An in-depth study of the intramolecular [5 + 2] photocycloaddition of maleimides using tunable UV lasers has demonstrated that the peak in quantum yield and rate both occur at wavelengths some 50 nm red shifted from the maxima observed in the UV spectra. A detailed explanation for these findings using time-dependent DFT calculations is presented, and the implications for a previously adopted mechanism are discussed. © 2007 American Chemical Society.

AB - (Chemical Equation Presented) An in-depth study of the intramolecular [5 + 2] photocycloaddition of maleimides using tunable UV lasers has demonstrated that the peak in quantum yield and rate both occur at wavelengths some 50 nm red shifted from the maxima observed in the UV spectra. A detailed explanation for these findings using time-dependent DFT calculations is presented, and the implications for a previously adopted mechanism are discussed. © 2007 American Chemical Society.

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U2 - 10.1021/jo062316g

DO - 10.1021/jo062316g

M3 - Article (Academic Journal)

C2 - 17253755

VL - 72

SP - 1449

EP - 1457

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -

Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition: A dual approach using tunable UV lasers and time-dependent DFT

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A UNIQUE HIGH POWER TUNABLE UV LASER FACILITY FOR SYNTHETIC PHOTOCHEMISTRY

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Reaction optimization and mechanism in maleimide [5 + 2] photocycloaddition: A dual approach using tunable UV lasers and time-dependent DFT

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A UNIQUE HIGH POWER TUNABLE UV LASER FACILITY FOR SYNTHETIC PHOTOCHEMISTRY

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