Sommelet reaction

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The Sommelet reaction is an organic reaction in which a benzyl halide is converted to an aldehyde by action of hexamine and water.[1][2][3]

The Sommelet reaction

The reaction is formally an oxidation of the carbon. In the related Kröhnke aldehyde synthesis,[4][5] the oxidizing reagent is a combination of pyridine and p-nitrosodimethylaniline.

The reaction has proved useful for the preparation of aldehydes from amines and halides. Various types of aromatic, heterocyclic, some aliphatic aldehydes and amines have been prepared.

References[edit]

  1. ^ Marcel Sommelet (1913). "Sur un mode de décomposition des halogénoalcoylates d'hexaméthylène – tétramine". Compt. Rend. 157: 852–854. 
  2. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7 
  3. ^ For an example see: Organic Syntheses, Coll. Vol. 4, p. 918 (1963); Vol. 33, p. 93 (1953). http://www.orgsynth.org/orgsyn/pdfs/CV4P0918.pdf
  4. ^ Über alpha-Keto-aldonitrone und eine neue Darstellungsweise von alpha-Keto-aldehyden Fritz Kröhnke, Erich Börner Berichte der deutschen chemischen Gesellschaft (A and B Series) Volume 69 Issue 8, Pages 2006–16 1936doi:10.1002/cber.19360690842
  5. ^ Über Nitrone, II. Mitteil. F. Kröhnke, Berichte der deutschen chemischen Gesellschaft (A and B Series) Volume 71 Issue 12, Pages 2583–93 1938 doi:10.1002/cber.19380711225