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Issue 4, 2012
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The effects of H-bonding and sterics on the photoreactivity of a trimethyl butyrophenone derivative

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Abstract

The irradiation of ester 1 in methanol and chloroform does not yield any photoproducts, whereas the photolysis of 1 in dry argon-saturated benzene produces cyclobutanol 4, which is converted to lactone 5 by the addition of HCl. Laser-flash photolysis of ester 1 demonstrates that 1 undergoes intramolecular H-atom abstraction to form the biradical 2 (λmax ∼ 310 nm, τ = 200 ns, benzene), which intersystem crosses to photoenols, Z-3 (λmax ∼ 380 nm, τ = 30–60 μs, benzene) and E-3 (λmax ∼ 380 nm, τ = 11 ms, benzene). Density functional theory calculations were performed to support the proposed mechanism for forming cyclobutanol 4 and to explain how steric demand facilitates photoenol E-3 to form cyclobutanol 4 rather than lactone 5.

Graphical abstract: The effects of H-bonding and sterics on the photoreactivity of a trimethyl butyrophenone derivative

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Article information


Submitted
04 Oct 2011
Accepted
20 Feb 2012
First published
12 Mar 2012

Photochem. Photobiol. Sci., 2012,11, 744-751
Article type
Paper

The effects of H-bonding and sterics on the photoreactivity of a trimethyl butyrophenone derivative

Q. Li, J. Sankaranarayanan, M. Hawk, V. T. Tran, J. L. Brown and A. D. Gudmundsdottir, Photochem. Photobiol. Sci., 2012, 11, 744
DOI: 10.1039/C2PP05330F

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