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Mass Spectrometry of Benzyne and Cyclopentadienylideneketene

Thomas Monsandl ^A , Graham Macfarlane ^A , Robert Flammang ^B and Curt Wentrup ^A ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

^B Laboratoire de Chimie Organique, Centre de Spectrométrie de Masse, Université de Mons-Hainaut, B-7000 Mons, Belgium.

^C Corresponding author. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 63(7) 1076-1083 https://doi.org/10.1071/CH09640
Submitted: 9 December 2009 Accepted: 20 April 2010 Published: 15 July 2010

Abstract

The formation of cyclopentadienylideneketene 2 and benzyne 1 in flash vacuum thermolysis reactions is investigated by on-line mass spectrometry. Compounds 13, 14, and 15 all afford ketene 2, which decomposes to benzyne and CO in the high-temperature regime. Cyclopentadienylideneketene 2 is stable on the microsecond time-scale of neutralization-reionization experiments. Collisional activation mass spectrometry of m/z 76 from 14, 15, and 5 indicates that the C₆H₄^•+ ions most likely undergo ring opening in the mass spectrometer.

Acknowledgements

This work was supported by the Australian Research Council and the Deutsche Forschungsgemeinschaft (Postdoctoral Fellowship for T.M.). The mass spectrometers were purchased with funds provided by The Vice-Chancellor of The University of Queensland (Kratos) and the Fonds National de la Recherche Scientifique, Brussels (Micromass).

References

[1] (a) For calculations on cyclopentadienylideneketene 2 see: Radziszewski J. G., Kaszynski P., Friedrichsen A., Abildgaard J., Collect. Czech. Chem. Commun. 1998, 63, 1094. doi:10.1135/CCCC19981094
       (b) A. C. Scheiner, H. F. Schaefer, J. Am. Chem. Soc. 1992, 114, 4758.
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