Talk:Corey–Fuchs reaction

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How do we know that the reaction happens by a carbene intermediate? I haven't been able to find anything that supports that mechanism. 130.225.0.251 (talk) 19:20, 14 December 2012 (UTC)

If you start from Ar-C(O)D, you get 50% deuterium incorporation for the terminal alkyne. This is consistent with a carbene mechanism; deprotonation/beta-elimination (of LiBr) or Li-Br exchange/beta elimination (of DBr) would both remove the deuterium. I assume the 50% H incorporation is caused by deprotonation of the acidic terminal Alkyne-D by the excess BuLi (they use 2 equiv.). Source: {{cite journal|last1=Sahu|first1=Bichismita|last2=Muruganantham|first2=Rajendran|last3=Namboothiri|first3=Irishi N. N.|title=Synthetic and Mechanistic Investigations on the Rearrangement of 2,3-Unsaturated 1,4-Bis(alkylidene)carbenes to Enediynes|journal=European Journal of Organic Chemistry|volume=2007|issue=15|year=2007|pages=2477–2489|issn=1434193X|doi=10.1002/ejoc.200601137}} Cato82 (talk) 18:15, 16 February 2016 (UTC)