Electrophilic 1,2-addition of oxoammonium salts to olefins

Chemistry Letters

Volumn , Issue 9, 1999, Pages 937-938

  Takata, Toshikazu ^b   Tsujino, Yasunori ^b   Nakanishi, Saburo ^b   Nakamura, Kazuaki ^a   Yoshida, Eri ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033476369     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.937     Document Type: Article

References (21)

1. Reviews see: M. Yamaguchi, T. Miyazawa, T. Takata, and T. Endo, Pure Appl. Chem., 62, 217 (1990); T. Endo and T. Miyazawa, Yuki Gosei Kagaku Kyokaishi, 44, 1134 (1986); J.M. Bobbitt and M.C.L. Flores, Heterocycles, 27, 509 (1988).
2. Reviews see: M. Yamaguchi, T. Miyazawa, T. Takata, and T. Endo, Pure Appl. Chem., 62, 217 (1990); T. Endo and T. Miyazawa, Yuki Gosei Kagaku Kyokaishi, 44, 1134 (1986); J.M. Bobbitt and M.C.L. Flores, Heterocycles, 27, 509 (1988).
3. Reviews see: M. Yamaguchi, T. Miyazawa, T. Takata, and T. Endo, Pure Appl. Chem., 62, 217 (1990); T. Endo and T. Miyazawa, Yuki Gosei Kagaku Kyokaishi, 44, 1134 (1986); J.M. Bobbitt and M.C.L. Flores, Heterocycles, 27, 509 (1988).
4. M. Yamaguchi, T. Takata, and T. Endo, Tetrahedron Lett., 29, 5671 (1988); M. Yamaguchi, T. Takata, and T. Endo, J. Org. Chem., 55, 1490 (1990); J.M. Bobbitt, J. Org. Chem., 63, 9367 (1998) and references cited therein.
5. M. Yamaguchi, T. Takata, and T. Endo, Tetrahedron Lett., 29, 5671 (1988); M. Yamaguchi, T. Takata, and T. Endo, J. Org. Chem., 55, 1490 (1990); J.M. Bobbitt, J. Org. Chem., 63, 9367 (1998) and references cited therein.
6. M. Yamaguchi, T. Takata, and T. Endo, Tetrahedron Lett., 29, 5671 (1988); M. Yamaguchi, T. Takata, and T. Endo, J. Org. Chem., 55, 1490 (1990); J.M. Bobbitt, J. Org. Chem., 63, 9367 (1998) and references cited therein.
7. T. Miyazawa and T. Endo, J. Org. Chem., 50, 3930 (1985).
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9. V.A. Golubev and E.V. Kobylyanskii, J. Org. Chem. USSR, 8, 2657 (1972); V.I. Rozenberg, V.K. Piotrovskii, V.A. Golubev, K.I. Gron, V.A. Nikanorov, Yu.G. Bundel, and O.A. Reutov, Bull. Akad. Sci. USSR, Chem. Ser., 24, 2508 (1975).
10. For examples: E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827; E. Yoshida, T. Ishizone, A. Hirao, S. Nakahama, T. Takata, and T. Endo, Macromolecules, 27, 3119 (1994); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 26, 554 (1993); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 25, 7282 (1992).
11. For examples: E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827; E. Yoshida, T. Ishizone, A. Hirao, S. Nakahama, T. Takata, and T. Endo, Macromolecules, 27, 3119 (1994); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 26, 554 (1993); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 25, 7282 (1992).
12. For examples: E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827; E. Yoshida, T. Ishizone, A. Hirao, S. Nakahama, T. Takata, and T. Endo, Macromolecules, 27, 3119 (1994); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 26, 554 (1993); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 25, 7282 (1992).
13. For examples: E. Yoshida, T. Takata, T. Endo, T. Ishizone, A. Hirao, and S. Nakahama, Chem. Lett., 1994, 1827; E. Yoshida, T. Ishizone, A. Hirao, S. Nakahama, T. Takata, and T. Endo, Macromolecules, 27, 3119 (1994); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 26, 554 (1993); E. Yoshida, T. Takata, and T. Endo, Macromolecules, 25, 7282 (1992).
14. E. Yoshida, K. Nakamura, T. Takata, and T. Endo, J. Polym. Sci., Part A: Polym. Chem., 31, 1505 (1993).
15. T. Miyazawa, T. Endo, S. Shiihashi, and M. Okawara, J. Org. Chem., 50, 1332 (1985).
16. 3) δ 5.60 (t, 1H), 4.13 (d, 2H), 3.35 (d, 2H), 3.28 (s, 3H), 3.80 ∼ 2.90 (m, 1H), 2.00 (d, 2H), 1.76 (d, 2H), 1.62 (m, 1H), 1.27 (s, 6H), 1.20 (s, 6H), 0.93 (d, 6H).
17. 2
18. 4: C, 65.21; H, 11.25; N, 4.23%.
19. E.G. Rozantsev, "Free Nitroxyl Radicals," ed by H. Ulrich, Plenum Press, New York (1970).
20. For example, K. Saigo, K. Kudo, Y. Hashimoto, H. Kimoto, and M. Hasegawa, Chem. Lett., 1990, 941.
21. Y. Shishido and C. Kobayashi, J. Org. Chem., 57, 2876 (1992).