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Australian Journal of Chemistry Australian Journal of Chemistry Society
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RESEARCH FRONT

Flash Vacuum Pyrolytic Generation of Arynes – in Retrospect

Roger F. C. Brown A B
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A Formerly of the Department of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B Present address: 5 York Street, Prahran, Vic. 3181, Australia. Email: rogerbrown@netspace.net.au

Australian Journal of Chemistry 63(7) 1002-1006 https://doi.org/10.1071/CH10086
Submitted: 16 February 2010  Accepted: 22 February 2010   Published: 15 July 2010

Abstract

The development of the chemistry of benzyne and of arynes under flash vacuum pyrolytic conditions was strongly influenced by a parallel study of the chemistry of propadienones, and by the discovery of the acetylene/methylenecarbene rearrangement. A limited range of typical aryne reactions studied at The Australian National University and at Monash University from 1965 to 1996 is described, and pathways of aryne formation are considered.


Acknowledgements

It is a pleasure to thank Frank Eastwood for more than 20 years of fruitful collaboration, and our coworkers for their skilled and enthusiastic contributions; some key experimentalists are named within this account. Much of this work was supported by the Australian Research Council.


References


[1]   Hoffmann R. W., Dehydrobenzene and Cycloalkynes 1967 (Academic Press: New York, NY).

[2]   (a) R. F. C. Brown, R. K. Solly, Chem. Ind. 1965,  1462.
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