Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of α-acetoxy and α-alkoxy azo compounds

Tetrahedron

Volumn 52, Issue 47, 1996, Pages 14673-14688

  Barton, Derek H R ^a   Jaszberenyi, Joseph Cs ^a,b   Liu, Wansheng ^a   Shinada, Tetsuro ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030592698     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00940-4     Document Type: Article

References (59)

1. 1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd Ed. John Wiley & Sons: N. Y., 1991; pp. 212-214 and references therein.
2. (b) Smith, P. A. S. Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds; Benjamin/Cummings: Reading, 1983.
3. 2. (a) Zeng, H.; Chen, Z.-C. Syn. Commun. 1993, 23, 2497.
4. (b) Barton, D. H. R.; Lester, D. J.; Ley, S. V. J. Chem. Soc., Pekin Trans. I 1980, 1212.
5. (c) Caglioti, L.; Gasparrini, F. Synthesis 1979, 207.
6. (d) Sacks, C. E.; Fuchs, P. L. Synthesis 1976, 456.
7. (e) Maynez, S. R., Pelavin, L.; Erker, G. J. Org. Chem. 1975, 40, 3302.
8. 3. Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735.
9. 4. (a) Creary, X. Org. Synth. 1984, 64, 207.
10. (b) Shapiro, R. H. Org. React. 1976, 23, 405.
11. 5. (a) Fischer, E. Chem. Ber. 1887, 20, 825.
12. (b) Mester, L.; Messmer, A. in Methods in Carbohydrate Chemistry, Vol. 2: Reactions of Carbohydrates; Whistler R. L.; Wolfrom, M. L. Eds; Academic Press: N.Y., 1963; p. 117. and references there cited.
13. 6. (a) Barton, D. H. R.; Okano, T.; Parekh, S. I. Tetrahedron 1991, 47, 1823.
14. (b) Barton, D. H. R.; Lester, D. J. ; Ley, S. V. J. Chem. Soc., Perkin Trans. I 1980, 1212.
15. (c) Griffith, J.; Hawkins, C. J. Chem. Soc., Perkin Trans. II 1977, 747.
16. 7. For reviews on hypervalent organoiodine compounds: (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
17. (b) Moriarty, R. M.; Vaid, R. K., Koser, G. F. Synlett 1990, 365.
18. 8. Barton, D. H. R.; Jaszberenyi, J. Cs.; Shinada, T. Tetrahedron Lett. 1993, 34, 7191.
19. 9. (a) For KDO chemistry: Unger, F. M. Adv. in Carbohydr. Chem. Biochem. 1981, 38, 323.
20. (b) Barton, D. H. R.; Jaszberenyi, J. Cs.; Liu, W.; Shinada, T. Tetrahedron 1996, 52, 2717.
21. 10. (a) Gillis, B. T.; LaMantagne, M. P. J. Org. Chem. 1968, 33, 762.
22. (b) Gillis, B. T., Schimmel, K. F. J. Org. Chem. 1967, 32, 2865.
23. (c) Gillis, B. T., Schimmel, K. F. J. Org. Chem. 1962, 27, 413.
24. 11. (a) Butler, R. N.; Scott, F. L., O'Mahony, T. A. F. Chem. Rev. 1973, 73, 93 and references cited therein.
25. (b) Iffland, D. C.; Salisbury, L.; Schafer, W. R. J. Am. Chem. Soc. 1961, 83, 747.
26. (c) Bornstein, J.; Skarlos, L. J. Org. Chem. 1970, 35, 1230.
27. (d) Butler, R. N.; King, W. B. J. Chem. Soc., Perkin Trans. I 1980, 1212.
28. (e) Butler, R. N.; King, W. B. J. Chem. Soc., Perkin Trans. I 1977, 282.
29. (f) Harrison, M. J.; Norman, R. O. C.; Gladstone, W. A. F. J. Chem. Soc. (C) 1967, 735.
30. 12. Butler, R. N.; Moris, G. J.; O'Donohue, A. M. J. Chem. Soc., Perkin Trans. II 1981, 1243.
31. 13. (a) Gladstone, W. A. F.; Norman, R. O. C. J. Chem. Soc. (C) 1966, 1527.
32. (b) Gale, D. J.; Wilshire, J. F. K. Aust. J. Chem. 1973, 26, 2683.
33. 14. (a) Ishibashi, F.; Nashima, T.; Nishino, J.; Kobayashi, I.; Ichihara, Y.; Kitagawa, Y.; Sasaki, S.; Yoshikawa, M.; Matsuoka, A.; Yamamoto, K. Bull. Chem. Soc. Jpn. 1986, 59, 73.
34. (b) Murakarni, Y.; Yokoyama, Y.; Miura, T.; Hirasawa, H.; Kamimura, Y.; Izaki, M. Heterocycles 1984, 22, 1211.
35. 15. (a) Severin, T.; Supp, W.; Manninger, G. Chem. Ber. 1979, 112, 3013.
36. (b) Newkome, G. R.; Fishel, D. L. J. Org. Chem. 1966, 31, 677.
37. 16. Ciganek, E. J. Org. Chem. 1970, 35, 862.
38. 17. (a) Moriarty, R. M.; Berglund, B. A.; Rao, S. C. M. Synthesis 1993, 318.
39. (b) Yang, R.-Y.; Dai, L.-X. J. Org. Chem. 1993, 55, 3381.
40. 18. Prakash, O. Aldrichimica Acta 1995, 28, 63.
41. 19. (a) Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1983, 48, 65.
42. (b) Witkop, B.; Kissman, H. M. J. Am. Chem. Soc. 1953, 75, 1975.
43. (c) Bellamy, A. J., Guthrie, R. D. J. Chem. Soc. 1965, 2788.
44. 20. Barton, D. H. R.; Elliott, J. D.; Géro, S. D. J. Chem. Soc., Perkin Trans. I 1982, 2085.
45. 21. (a) Kosower, E. M. Acc. Chem. Res. 1971, 4, 193.
46. (b) Galland, R.; Heesing, A.; Kaiser, B.-U. Liebigs Ann. Chem. 1976, 97.
47. (c) Porter, N. A.; Dubay, G. R., Green, J. G. J. Am. Chem. Soc. 1978, 100, 920.
48. (d) Evanochko, W. T.; Shevlin, P. B. J. Am. Chem. Soc. 1978, 100, 6428.
49. 22. (a) Barthel, W. F.; Leon, J.; Hall, S. A. J. Org. Chem. 1954, 19, 485.
50. (b) Rubottom, G. M.; Gruber, J. M.; Marrero, R.; Juve, Jr., H. D., Kim, C. W. J. Org. Chem. 1983, 48, 4940.
51. 23. Barton, D. H. R.; Jaszberenyi, J. Cs.; Leßmann, K.; Timár, T. Tetrahedron 1992, 48, 8881.
52. 24. (a) Murray, R. W.; Trozzolo, A. M. J. Org. Chem. 1961, 26, 3109.
53. (b) For a review on diazo chemistry: Regitz, M. Synthesis 1972, 351.
54. 25. Neeman, M.; Modiano, A.; Shor, Y. J. Org. Chem. 1956, 21, 671.
55. 26. (a) Yoneda, N.; Fukuhara, T., Mizokami, T.; Suzuki, A. Chem. Lett. 1991, 459.
56. (b) For a recent review on the dediazoniation of arenediazonium ions: Zollinger, H. Diazo Chemistry I: Aromatic and Heteroaromatic Compounds; VCH: Weiheim/N.Y., 1994, pp. 161-288.
57. 27. Bruce, W. F. Org. Synth., Coll. Vol. 2 1943, 139.
58. 28. Cappon, J. J.; Baart, J.; van der Walle, G. A. M., Raap, J.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1991, 110, 158.
59. 29. Benincori, T.; Pagani, S. B.; Fusco, R.; Sannicolo, F. J. Chem. Soc., Perkin Trans. 1 1988, 2721.