Preparation of novel cyclic hypervalent iodine(III) compounds having azido, cyano, and nitrato ligands

Heterocycles

Volumn 42, Issue 1, 1996, Pages 47-51

  Akai, Shuji ^a   Okuno, Takayuki ^a   Egi, Masahiro ^a   Takada, Takeshi ^a   Tohma, Hirofumi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001900397     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s11     Document Type: Article

References (31)

1. For recent reviews: R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, Inc., New York, 1992; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221.
2. For recent reviews: R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, Inc., New York, 1992; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221.
3. For recent reviews: R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, Inc., New York, 1992; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221.
4. For recent reviews: R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, Inc., New York, 1992; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221.
5. For recent reviews: R. M. Moriarty, R. K. Vaid, and G. F. Koser, Synlett, 1990, 365; R. M. Moriarty and R. K. Vaid, Synthesis, 1990, 431; Y. Kita, H. Tohma, and T. Yakura, Trends in Organic Chemistry, 1992, 3, 113; A. Varvoglis, "The Organic Chemistry of Polycoordinated Iodine,' VCH Publishers, Inc., New York, 1992; O. Prakash, N. Saini, and P. K. Sharma, Synlett, 1994, 221.
6. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
7. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
8. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
9. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
10. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
11. M. Arimoto, H. Yamaguchi, E. Fujita, Y. Nagao, and M. Ochiai, Chem. Pharm. Bull, 1989, 37, 3221; P. Magnus and J. Lacour, J. Am. Chem. Soc., 1992, 114, 767; P. Magnus, J. Lacour, and W. Weber, ibid., 1993, 115, 9347; F. Fontana, F. Minisci, Y. M. Yan, and L. Zhao, Tetrahedron Lett, 1993, 34, 2517; Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita, and M. Gyoten, Synlett, 1994, 427; P. Magnus, C. Hulme, and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501.
12. V. V. Zhdankin, C. M. Crittell, and P. J. Stang, Tetrahedron Lett., 1990, 31, 4821; V. V. Zhdankin, R. Tykwinski, B. L. Williamson, P. J. Stang, and N. S. Zefirov, ibid., 1991, 32, 733; P. J. Stang, V. V. Zhdankin, R. Tykwinski, and N. S. Zefirov, ibid., 1992, 33, 1419; V. V. Zhdankin, M. C. Scheuller, and P. J. Stang, ibid., 1993, 34, 6853.
13. V. V. Zhdankin, C. M. Crittell, and P. J. Stang, Tetrahedron Lett., 1990, 31, 4821; V. V. Zhdankin, R. Tykwinski, B. L. Williamson, P. J. Stang, and N. S. Zefirov, ibid., 1991, 32, 733; P. J. Stang, V. V. Zhdankin, R. Tykwinski, and N. S. Zefirov, ibid., 1992, 33, 1419; V. V. Zhdankin, M. C. Scheuller, and P. J. Stang, ibid., 1993, 34, 6853.
14. V. V. Zhdankin, C. M. Crittell, and P. J. Stang, Tetrahedron Lett., 1990, 31, 4821; V. V. Zhdankin, R. Tykwinski, B. L. Williamson, P. J. Stang, and N. S. Zefirov, ibid., 1991, 32, 733; P. J. Stang, V. V. Zhdankin, R. Tykwinski, and N. S. Zefirov, ibid., 1992, 33, 1419; V. V. Zhdankin, M. C. Scheuller, and P. J. Stang, ibid., 1993, 34, 6853.
15. V. V. Zhdankin, C. M. Crittell, and P. J. Stang, Tetrahedron Lett., 1990, 31, 4821; V. V. Zhdankin, R. Tykwinski, B. L. Williamson, P. J. Stang, and N. S. Zefirov, ibid., 1991, 32, 733; P. J. Stang, V. V. Zhdankin, R. Tykwinski, and N. S. Zefirov, ibid., 1992, 33, 1419; V. V. Zhdankin, M. C. Scheuller, and P. J. Stang, ibid., 1993, 34, 6853.
16. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
17. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
18. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
19. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
20. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
21. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
22. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
23. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
24. Five-membered cyclic hypervalent iodine(III) compounds have been shown to be more stable than their acyclic analogs: a) G. P. Baker, F. G. Mann, N. Sheppard, and A. J. Tetlow, J. Chem. Soc., 1965, 3721; b) H. J. Barber and M. A. Henderson, J. Chem. Soc. (C), 1970, 862; c) T. M. Balthazor, D. E. Godar, and B. R. Stults, J. Org. Chem., 1979, 44, 1447; d) R. L. Amey and J. C. Martin, ibid., 1979, 44, 1779; e) C. A. Panetta, S. M. Garlick, H. D. Durst, F. R. Longo, and J. R. Ward, ibid., 1990, 55, 5202; f) M. Ochiai, Y. Masaki, and M. Shiro, ibid., 1991, 56, 5511; g) M. Ochiai, T. Ito, Y. Masaki, and M. Shiro, J. Am. Chem. Soc., 1992, 114, 6269; h) G. F. Koser, G. Sun, C. W. Porter, and W. J. Youngs, J. Org. Chem., 1993, 58, 7310; R. A. Moss and H, Zonag, J. Am. Chem. Soc., 1994, 116, 4471.
25. Just before mailing this communication, a preparation of cyclic iodinanes having azido ligands was reported: V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, M. S. Formaneck, and J. T. Bolz, Tetrahedron Lett., 1994, 52, 9677.
26. Preparations of acyclic hypervalent iodine reagents having nitrato ligands were reported: Y. Yamada, K. Kashima, and M. Okawara, J. Polym. Sci., Polym. Lett. Ed., 1976, 14, 65; N. W. Alcock and R. M. Countryman, J. Chem. Soc, Dalton Trans., 1979, 851; J. Gallos, A. Varvoglis, N. W. Alcock, J. Chem. Soc., Perkin Trans, 1, 1985, 757 and references cited therein.
27. Preparations of acyclic hypervalent iodine reagents having nitrato ligands were reported: Y. Yamada, K. Kashima, and M. Okawara, J. Polym. Sci., Polym. Lett. Ed., 1976, 14, 65; N. W. Alcock and R. M. Countryman, J. Chem. Soc, Dalton Trans., 1979, 851; J. Gallos, A. Varvoglis, N. W. Alcock, J. Chem. Soc., Perkin Trans, 1, 1985, 757 and references cited therein.
28. Preparations of acyclic hypervalent iodine reagents having nitrato ligands were reported: Y. Yamada, K. Kashima, and M. Okawara, J. Polym. Sci., Polym. Lett. Ed., 1976, 14, 65; N. W. Alcock and R. M. Countryman, J. Chem. Soc, Dalton Trans., 1979, 851; J. Gallos, A. Varvoglis, N. W. Alcock, J. Chem. Soc., Perkin Trans, 1, 1985, 757 and references cited therein.
29. M. G. Voronkov, E. A. Maletina, and V. K. Roman, Zh. Obshch. Khim., 1975, 45, 1900.
30. +-Me).
31. Selected bond distances (A) and angles (deg) for 7 and 8 are as follows: 7, C1-I1 2.13(1), O1-I1 2.218(9), I1-C8 2.11(1), C9-I2 2.11(1), O3-I2 2.221(9), I2-C16 2.13(2), C8-I1-C1 89.4(5), C8-I1-O1 166.6(5), C1-I1-O1 77.2(4), C9-I2-C16 88.8(5), C9-I2-O3 77.0(4), C16-I2-O3 165.8(5); 8, C1-I2.08(2), O1-I 2.00(2), I-O2 2.26(2), O1-I-C1 81.9(8), O1-I-O2 165.9(8), C1-I-O2 84.1(7).