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Blaise ketone synthesis

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Blaise ketone synthesis
Named after Edmond Blaise
Reaction type Coupling reaction

The Blaise ketone synthesis (named after Edmond Blaise) is the chemical reaction of acid chlorides with organozinc compounds to give ketones.[1][2]

The Blaise ketone synthesis
The Blaise ketone synthesis

The reaction also works with organocuprates.[3][4]

Reviews have been written.[5][6]

Variations

Blaise-Maire reaction

The Blaise-Maire reaction is the Blaise ketone synthesis using β-hydroxy acid chlorides to give β-hydroxyketones, which are converted into α,β-unsaturated ketones using sulfuric acid.[7]

See also

References

  1. ^ Blaise, E. E.; Koehler, A. (1910). "Synthèse au moyen des dérivés organo-métalliques mixtes du zinc (II)". Bull. Soc. Chim. Fr. 7: 215–227.
  2. ^ Blaise, E. E. (1911). "Sur les dérivés organo-métalliques mixtes du zinc et leur emploi dans la synthèse organique". Bull. Soc. Chim. Fr. 9: 1.
  3. ^ Posner, G. H.; Whitten, C. E. (1976). "Secondary and Tertiary Alkyl Ketones from Carboxylic Acid Chlorides and Lithium Phenylthio(Alkyl)Cuprate Reagents: tert-Butyl Phenyl Ketone". Organic Syntheses. 55: 122; Collected Volumes, vol. 6, p. 248.
  4. ^ Fujisawa, T.; Sato, T. (1988). "Ketones from Carboxylic Acids and Grignard Reagents: Methyl 6-Oxodecanoate". Organic Syntheses. 66: 116; Collected Volumes, vol. 8, p. 441.
  5. ^ Cason, J. (1947). "The Use of Organocadmium Reagents for the Preparation of Ketones". Chem. Rev. 40 (1): 17. doi:10.1021/cr60125a002. PMID 20287882.
  6. ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Organic Reactions. 8: 29. doi:10.1002/0471264180.or008.02. ISBN 0471264180.
  7. ^ Blaise, E. E.; Maire, M. (1907). "Synthèse au moyen des dérivés organo-métalliques mixtes du zinc. Cétones non saturées αβ-acycliques". Compt. Rend. 145: 73-75.