Sommelet reaction

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 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

  1. ^ Marcel Sommelet (1913). "Sur un mode de décomposition des halogénoalcoylates d'hexaméthylène - tétramine". Compt. rend. 157: 852–854. http://gallica.bnf.fr/ark:/12148/bpt6k31103/f852.table. 
  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 - 2016 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 - 2593 1938 doi:10.1002/cber.19380711225