The Oxidation of Secondary Alcohols to Ketones with Trichloroisocyanuric Acid

References

• Hiegel , G. A. and Peyton , K. B. 1985 . Synth. Commun. , 15 ( 5 ) : 385
   Web of Science ®Google Scholar
• Back , T. G. , Chau , J. H.-L. , Dyck , B. P. and Gladstone , P. L. 1991 . Can. J. Chem. , 69 ( 9 ) : 1482
   Web of Science ®Google Scholar
• Walters , T. R. , Zajac , W. W. Jr. and Woods , J. M. 1991 . J. Org. Chem. , 56 : 316
   Web of Science ®Google Scholar
• Mukawa , F. 1957 . Nippon Kagaku Zasshi , 78 : 450
   Google Scholar
• 1959 . Chem. Abstr. , 53 : 5338a A previous report of small scale (0.5 g or less) oxidation of several steroid and two terpene alcohols using 1 has appeared. This study was of limited scope and a general oxidation procedure was not developed.
   Google Scholar
• Hiegel , G. A. , Abdala , M. H. , Burke , S. V. and Beard , D. P. 1987 . J. Chem. Ed. , 64 ( 2 ) : 156
   Web of Science ®Google Scholar
• Stevens , R. V. , Chapman , K. T. and Weller , H. N. 1980 . J. Org. Chem. , 45 : 2030
   Web of Science ®Google Scholar
• Radhakrishnamurti , P. S. and Rath , N. K. 1985 . Indian J. Chem. , 24A : 300
   Google Scholar
• Vasudevan , K. S. and Venkatasubramanian , N. 304 ibid.
   Google Scholar
• Acetone is also chlorinated, but the chloro compounds are effectively destroyed during the workup.
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• Eaton , E. 1964 . Mfg. Chemist and Aerosol News , 35 ( 12 ) : 45 As with other strong oxidizing agents, 1 should be added to the solvent rather than the solvent to 1 otherwise a violent reaction could occur. An excess of 1 was used because some is lost due to side reactions, and it has been reported to be about 90% reactive as determined by a thiosulfate titration of the iodine liberated on reaction of 1 with iodide. See
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• If the test had been positive, then saturated NaHSO3 solution would have been added, and the solution stirred for a few minutes and tested again. This procedure would have been repeated until the test was negative.
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