Issue 10, 2005
From the journal:

Photochemical & Photobiological Sciences

Photocyclization of a conformationally constrained 2-vinylbiphenyl

Meledathu C. Sajimona  and  Frederick D. Lewis*a  

* Corresponding authors

a Department of Chemistry, Northwestern University, Evanston, Illinois, USA
E-mail: lewis@chem.northwestern.edu

Abstract

The synthesis and photochemical behavior of a rigid analog of syn-2-vinylbiphenyl are reported. This analog undergoes quantitative conversion to a tetrahydrobenzanthracene derivative upon irradiation in fluid solution. Product formation is proposed to occur via photocyclization to yield an unstable intermediate followed by an intramolecular thermal hydrogen shift. The intermediate can be observed upon irradiation at low temperature either in a rigid glass or in liquid propane solution. The temperature dependence of its decay is indicative of a tunneling mechanism for the hydrogen shift process.

Graphical abstract: Photocyclization of a conformationally constrained 2-vinylbiphenyl

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Article information

DOI
https://doi.org/10.1039/B511270B
Article type
Communication
Submitted
09 Aug 2005
Accepted
25 Aug 2005
First published
05 Sep 2005

Photochem. Photobiol. Sci., 2005,4, 789-791

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Photocyclization of a conformationally constrained 2-vinylbiphenyl

M. C. Sajimon and F. D. Lewis, Photochem. Photobiol. Sci., 2005, 4, 789 DOI: 10.1039/B511270B

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