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Allenes
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== History == For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with.<ref name=":0">The Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982.</ref><ref name=":2">{{Cite journal|last=Taylor|first=David R.|date=1967-06-01|title=The Chemistry of Allenes|url=https://pubs.acs.org/doi/abs/10.1021/cr60247a004|journal=Chemical Reviews|language=en|volume=67|issue=3|pages=317–359|doi=10.1021/cr60247a004|issn=0009-2665|url-access=subscription}}</ref> Reportedly,<ref name=":1">{{Cite journal|last1=Hoffmann-Röder|first1=Anja|last2=Krause|first2=Norbert|date=2004-02-27|title=Synthesis and Properties of Allenic Natural Products and Pharmaceuticals|url=https://onlinelibrary.wiley.com/doi/10.1002/anie.200300628|journal=Angewandte Chemie International Edition|language=en|volume=43|issue=10|pages=1196–1216|doi=10.1002/anie.200300628|pmid=14991780|issn=1433-7851|url-access=subscription}}</ref> the first synthesis of an allene, [[glutinic acid]], was performed in an attempt to prove the non-existence of this class of compounds.<ref>{{Cite journal|last1=Burton|first1=B. S.|last2=von Pechmann|first2=H.|date=January 1887|title=Ueber die Einwirkung von Chlorphosphor auf Acetondicarbonsäureäther|url=https://onlinelibrary.wiley.com/doi/10.1002/cber.18870200136|journal=Berichte der Deutschen Chemischen Gesellschaft|language=de|volume=20|issue=1|pages=145–149|doi=10.1002/cber.18870200136}}</ref><ref>{{Cite journal|last1=Jones|first1=E. R. H.|last2=Mansfield|first2=G. H.|last3=Whiting|first3=M. C.|date=1954|title=Researches on acetylenic compounds. Part XLVII. The prototropic rearrangements of some acetylenic dicarboxylic acids|url=http://xlink.rsc.org/?DOI=jr9540003208|journal=Journal of the Chemical Society (Resumed)|language=en|pages=3208–3212|doi=10.1039/jr9540003208|issn=0368-1769|url-access=subscription}}</ref> The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone.<ref>Data from the [[Web of Science]] database.</ref> These compounds are not just interesting intermediates but synthetically valuable targets themselves; for example, over 150 natural products are known with an allene or cumulene fragment.<ref name=":1" />
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