Unexpected formation of β-(phenylseleno)alkyl nitrates by the reaction of alkenes with the diselenide-nitrogen dioxide couple

Chemical Communications

Volumn , Issue 4, 1996, Pages 475-476

  Han, Li Biao ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

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EID: 1842435266     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000475     Document Type: Article

References (28)

1. 2 in organic synthesis see: E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314; M. Nakata and H. Frei, J. Am. Chem. Soc., 1992, 114, 1363; H. Suzuki, T. Ishibashi, T. Murashima and K. Tsukamoto, Tetrahedron, 1991, 32, 6591; D. H. Giamalva, G. B. Kenion, D. F. Church and W. A. Pryor, J. Am. Chem. Soc., 1987, 109, 7059. See also: The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1986, vols. 1 and 2.
2. 2 in organic synthesis see: E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314; M. Nakata and H. Frei, J. Am. Chem. Soc., 1992, 114, 1363; H. Suzuki, T. Ishibashi, T. Murashima and K. Tsukamoto, Tetrahedron, 1991, 32, 6591; D. H. Giamalva, G. B. Kenion, D. F. Church and W. A. Pryor, J. Am. Chem. Soc., 1987, 109, 7059. See also: The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1986, vols. 1 and 2.
3. 2 in organic synthesis see: E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314; M. Nakata and H. Frei, J. Am. Chem. Soc., 1992, 114, 1363; H. Suzuki, T. Ishibashi, T. Murashima and K. Tsukamoto, Tetrahedron, 1991, 32, 6591; D. H. Giamalva, G. B. Kenion, D. F. Church and W. A. Pryor, J. Am. Chem. Soc., 1987, 109, 7059. See also: The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1986, vols. 1 and 2.
4. 2 in organic synthesis see: E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314; M. Nakata and H. Frei, J. Am. Chem. Soc., 1992, 114, 1363; H. Suzuki, T. Ishibashi, T. Murashima and K. Tsukamoto, Tetrahedron, 1991, 32, 6591; D. H. Giamalva, G. B. Kenion, D. F. Church and W. A. Pryor, J. Am. Chem. Soc., 1987, 109, 7059. See also: The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1986, vols. 1 and 2.
5. 2 in organic synthesis see: E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314; M. Nakata and H. Frei, J. Am. Chem. Soc., 1992, 114, 1363; H. Suzuki, T. Ishibashi, T. Murashima and K. Tsukamoto, Tetrahedron, 1991, 32, 6591; D. H. Giamalva, G. B. Kenion, D. F. Church and W. A. Pryor, J. Am. Chem. Soc., 1987, 109, 7059. See also: The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, John Wiley & Sons, New York, 1986, vols. 1 and 2.
6. P. L. Feldman, O. W. Griffith and D. J. Stuehr, Chem. Eng. News, 1993, 71(51), 26; Y. Shibata, M. Morita and K. Fuwa, Adv. Biophys., 1992, 28, 31.
7. P. L. Feldman, O. W. Griffith and D. J. Stuehr, Chem. Eng. News, 1993, 71(51), 26; Y. Shibata, M. Morita and K. Fuwa, Adv. Biophys., 1992, 28, 31.
8. M. Iwamoto and H. Hamada, Catal. Today, 1991, 10, 57.
9. 2: S. Oae and K. Shinhama, Org. Prep. Proc. Int., 1983, 15, 167.
10. 2: S. Oae and K. Shinhama, Org. Prep. Proc. Int., 1983, 15, 167.
11. T. G. Back, Electrophilic Selenium Reactions, in Organoselenium Chemistry, ed. D. Liotta, John Wiley & Sons, New York, 1978, pp. 1-126.
12. K. Clusius and M. Vecchi, Helv. Chim. Acta, 1953, 36, 930.
13. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
14. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
15. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
16. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
17. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
18. For reviews on the preparation and synthetic utilities of β-hydroxyalkyl selenides see: ref. 5 and L. J. Clive, Tetrahedron, 1978, 34, 1049. For further applications of β-hydroxyalkyl selenides in organic synthesis, see also: T. Kametani, H. Kurobe, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1982, 1085; H. Nishiyama, T. Kitajima, A. Yamamoto and K. Ito, J. Chem. Soc. Chem. Commun., 1982, 1232; J. L. Laboureur, W. Dumont and A. Krief, Tetrahedron Lett., 1984, 25, 4569; A. Krief, J. L. Laboureur and W. Dumont, Tetrahedron Lett., 1987, 28, 1549; S. Uemura, K. Ohe and N. Sugita, J. Chem. Soc., Perkin Trans. 1, 1990, 1697.
19. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
20. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
21. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
22. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
23. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
24. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
25. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
26. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
27. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.
28. β-Hydroxyalkyl selenides prepared by the hydroxyselenation of carbon-carbon unsaturated bonds: D. L. J. Clive, J. Chem. Soc., Chem. Commun., 1974, 100; H. J. Reich, J. Org. Chem., 1974, 39, 428; H. J. Reich and J. E. Trend, J. Org. Chem., 1976, 41, 2503; K. B. Sharpless and R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; D. Laber, A. Krief and L. Hevesi, Tetrahedron Lett., 1978, 3967; J. N. Denis, J. Vicens and A. Krief, Tetrahedron Lett., 1979, 2697; A. Toshimitsu, T. Aoai, H. Owada, S. Uemura and M. Okano, Tetrahedron, 1985, 41, 5301; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; P. S. Liu, V. E. Marques, J. A. Kelley and J. S. Driscoll, J. Org. Chem., 1980, 45, 5225; S. Torii, K. Uneyama and M. Ono, Tetrahedron Lett., 1980, 21, 2653.