Facile Conversion of Tosylhydrazones to Carbonyl Compounds by the Potassium Peroxymonosulfate-Acetone System

References

• Murray , R. W. 1989 . Chem. Rev. , 89 : 1187 (a), (b) Adam, W., Curci, R., and Edward, J. O., Acc. Chem. Res., 1989, 22, 205
   Web of Science ®Google Scholar
• Rosini , G. and Ballini , R. 1988 . Synthesis , : 833
   Web of Science ®Google Scholar
• Oda , R. , Mieno , M. and Hagashi , Y. 1967 . Tetrahedron Lett. , : 2363 (a), (b) Ho, T. L-. and Wong, C. M., J. Org. Chem., 1974, 39 3453. (c) Rosini, G., J. Org. Chem., 1974, 39, 3504. (d) Chandrasekhar, B. P., Suntharkar, S. V., and Telung, S. G., Chem. Ind. (London) 1975, 87. (e) Maynes, S. R., Pelavin, L., and Erker, G., J. Org. Chem., 1975, 40, 3302. (f) Sachs, C. E. and Fuchs, P. L., Synthesis, 1976, 456. (g) Olah, G. A., Welch, J., and Ho, T. L-., J. Am. Chem. Soc., 1978, 100, 5396. (h) Olah, G. A., Vankar, Y. D., and Prakash, G. K. S., Synthesis, 1979, 113. (i) Caglioti, L., Gasparrini, F., Misiti, D., and Palimieri, G., Synthesis, 1979, 207. (j) Laszlo, P. and Polla, E., Synthesis, 1985, 439
   Google Scholar
• Kim , Y. H. , Lee , H. K. and Chang , H. S. 1987 . Tetrahedron Lett. , 28 : 4285
   Google Scholar
• 4-Toluene sulfinic acid was actually oxidized to 4-toluene sulfonic acid under the same reaction conditions. The crude 4-toluene sulfonic acid was isolated and confirmed by its molecular peak in mass spectrum (m/z, 172, 11.4 %)
   Google Scholar
• Emmons , W. D. 1957 . J. Am. Chem. Soc. , 79 : 5739 (a), (b) Dinizo, S. E. and Watt, D. S., J. Am. Chem. Soc., 1975, 97, 6900. (c) Rasteffer, W. and Frost, J. W., Tetrahedron Lett., 1979, 3353. (d) Hata, Y. and Wtanabe, M, J. Am. Chem.Soc., 1979, 101 6671. (e) Rasteffer, W. H., Wagner, W. R., Findeis, M. A., J. Org. Chem., 1982, 47 419
   Web of Science ®Google Scholar
• Boyd , D. R. , Coulter , P. B. , McGuckin , M. R. , Sharma , N. D. , Jennings , W. B. and Wilson , V. E. 1990 . J. Chem. Soc., Perkin Trans. 1 , : 301
   Google Scholar
• Hiegel , G. A. and Peyton , K. B. 1985 . Synth. Commun. , 15 ( 5 ) : 385 and references cited therein, a), b) Back, T. G., Chau, J. H.-L., Dyck, B. P., and Gladstone, P. L., Can. J. Chem. 1991, 69 (9), 1482, c) Walters, T. R., Zajac, W. W., Jr., and Woods, J. M., J. Org. Chem. 1991, 56 316
   Web of Science ®Google Scholar
• Mukawa , F. 1957 . Nippon Kagaku Zasshi , 78 : 450 A previous report of small scale (0.5 g or less) oxidation of several steroid and two terpene alcohols using 1 has appeared, Chem. Abstr., 1959, 53 5338a. 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 a), b) Vasudevan, K. S. and Venkatasubramanian, N., ibid. 304
   Google Scholar
• Acetone is also chlorinated, but the chloro compounds are effectively destroyed during the workup
   Google Scholar
• Eaton , E. 1964 . Mfg. Chemist and Aerosol News , 35 ( 12 ) : 45 As with other strong oxidizing agents, I should be added to the solvent rather than the solvent to I otherwise a violent reaction could occur. An excess of I 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 I with iodide. See
   Google Scholar
• 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
   Google Scholar