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. Author manuscript; available in PMC: 2018 Jul 1.
Published in final edited form as: Synlett. 2017 Mar 10;28(12):2407–2421. doi: 10.1055/s-0036-1588778

Scheme 5.

Scheme 5

Thermodynamic cycles which divide tautomerization of carboxylic acid derivatives (KE) into separate steps for proton transfer at carbon [(Ka)CH] and at a heteroatom [1/(Ka)XH]. (A) Enolization at α–carbonyl carbon. (B) Tautomerization of acetonitrile.