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:



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 Letters 1968, 3363; J. C. Collins, W. W. Hess, Org. Syn. 52, 5 (1972); R. W. Ratcliffe, ibid. 55, 84 (1976). Cf. Jones Oxidation.