Hypervalent Iodine in Organic Synthesis

Accounts of Chemical Research

Volumn 19, Issue 8, 1986, Pages 244-250

  Moriarty, Robert M ^a   Prakash, Om ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845375869     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00128a003     Document Type: Article

References (30)

1. Barton, D. H. R. Chem, Br. 1973, 9,149. I would not like to neglect to mention that we are very poor in synthetic methods in organic chemistry. Most of the synthetic work is done with organic reactions of the type which have been known for a long time. If you know 20 organic reactions you probably know most of the steps used in synthetic work, particularly in industry, but I am quite sure there must be hundreds of other organic reactions to be discovered. We have not in the past thought about these problems in the right way. When we have been faced with a problem of effecting a chemical synthesis, we have sought known methods. We have not paused to think why we do not invent a new method every time. If we adopt this philosophy we are going to be extremely busy till the end of the century (a) trying to equal the enzymes, and (b) thinking up new ways of synthesis.
2. Martin, J. C. Science 1983, 221, 509. Also termed “nonmetallo-organic” compounds by Musher in ref 7.
3. Willgerodt, C. J. Prakt. Chem. 1886, 33, 154.
4. Willgerodt, C. Die Organischen Verbindugen mit Mehrwertigen Jod, Ferdinand Enke Verlag: Stuttgart, 1914.
5. For a review see Koser, G. F. “Halonium Ions” In The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 25.
6. For a reivew, see: Koser, G. F. “Hypervalent Halogen Compounds” In The Chemistry of Functional Groups, Supplement D; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 18.
7. Musher, J. I. Angew. Chem., Int. Ed. Eng. 1969, 8, 54.
8. For a discussion of hypervalency in organoiodine(III) compounds see Moriarty, R. M., in Tetrahedron Lett., in press. (9) Perozzi, E. F.; Michalak, R. S.; Figuly, G. D.; Stevenson, W. H., III; Dess, D. B.; Ross, M. R.; Martin, J. C. J. Org. Chem. 1981, 46, 1049.
9. Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101.
10. Farnham, W. B.; Calabrese, J. C. Abstracts of Papers 191st National Meeting of the American Chemical Society, New York, NY; American Chemical Society: Washington DC, 1986; INOR 258.
11. Moriarty, R. M.; Prakash, O.; Duncan, M. P. Synthesis 1985, 943.
12. Rebrovic, L.; Koser, G. F. J. Org. Chem. 1984, 49, 2462, and references cited therein. Koser's Reagent, marketed by Aldrich (catalog no. 30, 103–5).
13. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Dess-Martin periodinane, marketed by Aldrich (catalog no. 27462–3). (15) (a) Bell, R.; Morgan, K. J. J. Chem. Soc. 1960, 1209. (b) Siebert, H.; Handrich, M. J. Z. Anorg. Allg. Chem. 1976, 426, 173. (c) Schardt, B. C.; Hill, C-L. Inorg. Chem. 1983, 22, 1563.
14. Moriarty, R. M.; Hu, H.; Gupta, S. C. Tetrahedron Lett. 1981,22, 1283. (17) Hou, K. C. Ph.D. Thesis, University of Illinois at Chicago, Chicago, 1984.
15. Moriarty, R. M.; Hou, K. C. Tetrahedron Lett. 1984, 25, 691.
16. Moriarty, R. M.; Prakash, I.; Penmasta, R., unpublished result, 1985. (20) Moriarty, R. M.; Prakash, O., unpublished results.
17. Moriarty, R. M.; Prakash, O.; Karalis, P.; Prakash, I. Tetrahedron Lett. 1984, 25, 4745.
18. Moriarty, R. M.; Prakash, O.; Thachet, C. T.; Musallam, H. A. Heterocycles 1985, 23, 633.
19. (a) Bailey, E. J.; Barton, D. H. R.; Elks, J.; Templeton, J. F. J. Chem. Soc, 1962, 1578. (b) Gardner, J. N.; Carlon, F. E.; Gnoj, O. J. Org. Chem. 1968, 33, 3294. (c) Rubottom, G. M.; Vasques, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 4319. (d) Hassner, A.; Reuss, R. H.; Pinnick, H. W. J. Org. Chem. 1975, 40, 3427. (e) Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188. (f) McCormick, J. P.; Tomasik, W.; Johnson, M. W. Tetrahedron Lett. 1981, 22, 607. (g) Franklin, A. D.; Vishwakarma, L. C.; Billmers, J. M. J. Org. Chem. 1984, 49, 3241.
20. For a review, see: Mukaiyama, T. New Synthetic Methods', Weinheim: New York, 1979; Vol. 6, p 247.
21. Moriarty, R. M.; John, L. S.; Du, P. C. J. Chem. Soc., Chem. Commun. 1981, 641.
22. (a) Kamernitzky, A. V.; Turuta, A. M.; Fadeeva, T. M.; Istomina, Z. I. Synthesis 1985, 326. (b) Turuta, A. M.; Kamernitzky, A. V.; Fadeeva, T. M.; Zhulin, A. Z. Synthesis 1985, 1129. (27) Moriarty, R. M.; Prakash, O.; Freeman, W. A. J. Chem. Soc., Chem. Commun. 1984, 927.
23. Moriarty, R. M.; Prakash, O.; Musallam, H. A. J. Heterocycl. Chem. 1985 22 583
24. Moriarty, R. M.; Prakash, O. J. Org. Chem. 1985, 50, 151. (30) Moriarty, R. M.; Prakash, O.; Prakash, I.; Musallam, H. A. J. Chem. Soc., Chem. Commun. 1984, 1342.
25. (a) Moriarty, R. M.; Prakash, I.; Musallam, H. A. Tetrahedron Lett. 1984, 25, 5867. (b) Daum, S. J. Tetrahedron Lett. 1984, 25, 4725.
26. Moriarty, R. M.; Engerer, S. C.; Prakash, O.; Prakash, I.; Gill, U. S.; Freeman, W. A. J. Chem. Soc., Chem. Commun. 1985, 1715. (33) Moriarty, R. M.; Sultana, M. J. Am. Chem. Soc. 1985, 107, 4559.
27. Moriarty, R. M.; Sultana, M.; Ku, Y.Y. Y. J. Chem. Soc., Chem. Commun. 1985, 974.
28. Maletina, I. I.; Mironova, A. A.; Orda, V. V.; Yagupolskii, L. M. Synthesis 1983, 456.
29. Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
30. In this paper the periodic group notation in parentheses is in accord with recent actions by IUPAC and ACS nomenclature committees. A and B notation is eliminated because of wide confusion. Groups IA and IIA become groups 1 and 2. The d-transition elements comprise groups 3 through 12, and the p-block elements comprise groups 13 through 18. (Note that the former Roman number designation is preserved in the last digit of the numbering: e.g., III→3 and 13.)