Talk:Corey–Fuchs reaction

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)Reply

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: ^[1] Cato82 (talk) 18:15, 16 February 2016 (UTC)Reply

^ Sahu, Bichismita; Muruganantham, Rajendran; Namboothiri, Irishi N. N. (2007). "Synthetic and Mechanistic Investigations on the Rearrangement of 2,3-Unsaturated 1,4-Bis(alkylidene)carbenes to Enediynes". European Journal of Organic Chemistry. 2007 (15): 2477–2489. doi:10.1002/ejoc.200601137. ISSN 1434-193X.

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[SahuMuruganantham2007-1] Sahu, Bichismita; Muruganantham, Rajendran; Namboothiri, Irishi N. N. (2007). "Synthetic and Mechanistic Investigations on the Rearrangement of 2,3-Unsaturated 1,4-Bis(alkylidene)carbenes to Enediynes". European Journal of Organic Chemistry. 2007 (15): 2477–2489. doi:10.1002/ejoc.200601137. ISSN 1434-193X.

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