Matrix Isolation, Spectroscopic Characterization, and Photoisomerization of m-Xylylene

Patrik Neuhaus, Dirk Grote, and Wolfram Sander*
Lehrstuhl fr Organische Chemie II der Ruhr-Universitt, D-44780 Bochum, Germany
J. Am. Chem. Soc., 2008, 130 (10), pp 2993–3000
DOI: 10.1021/ja073453d
Publication Date (Web): February 16, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, wolfram.sander@rub.de

Abstract

Abstract Image

A new efficient synthesis of m-xylylene 1 is reported. The diradical 1 was trapped in argon matrices at 10 K and characterized by IR, UV−vis, and EPR spectroscopy. The syntheses reported before only allowed generation of 1 in organic glasses, and the spectroscopic identification was limited to fluorescence and EPR spectroscopy. Diradical 1 proved to be highly photolabile, and irradiation results in the formation of three isomeric hydrocarbons 7, 9, and 11 which could be identified by comparison of their IR spectra with the results of DFT calculations.

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History

  • Published In Issue March 12, 2008
  • Received May 15, 2007

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