357. Sarett Oxidation

Collins Oxidation

G. I. Poos, G. E. Arth, R. E. Beyler, L. H. Sarett, J. Am. Chem. Soc. 75, 422 (1953).

Oxidation of primary and secondary alcohols to aldehydes (and/or carboxylic acids) and ketones by means of CrO3-pyridine complex:

Chemical reaction

References

J. R. Holum, J. Org. Chem. 26, 4814 (1961); E. J. Kris, Chem. Ind. (London) 1961, 1834; V. I. Stenberg, R. J. Perkins, J. Org. Chem. 28, 323 (1963); P. G. Gassman, P. G. Pape, J. Org. Chem. 29, 160 (1964); H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 264-273. Mechanistic studies: F. Hasan, J. Rocek, J. Am. Chem. Soc. 97, 1444, 3762 (1975).

The Collins oxidation is characterized by a modified procedure (dichloromethane as solvent) that reliably oxidizes primary alcohols to aldehydes: J. C. Collins, Tetrahedron Lett. 1968, 3363; J. C. Collins, W. W. Hess, Org. Synth. 52, 5 (1972); R. W. Ratcliffe, ibid. 55, 84 (1976). Cf. Jones Oxidation.