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In reading about the Henry reaction in textbooks and online, I can't find any treatment of the reaction with the carbonyls of esters or acyl halides. I am imagining the reaction would be similar to the Grignard reaction, since both involve an attack on the carbonyl by a "carbanionic" species. I understand that the acyl halide and esters would be susceptible to hydrolysis, so perhaps that's the reason I can't find anything.

Has this reaction ever been performed on a carboxylic acid derivative as I have described?

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  • $\begingroup$ The dianion of nitroalkanes generated by KOtBu in DMSO has been reacted with N-acylbenzotriazoles to give alpha-nitroketones in the manner you are asking about. See Katritzky et al, J. Org. Chem. (2005) vol 70 9211 $\endgroup$ – Waylander Nov 9 '20 at 21:20
  • $\begingroup$ N-acyl, I hadn't even considered that one! Thanks, I will check out that paper! $\endgroup$ – Anger Density Nov 9 '20 at 21:40

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