Structure and properties of 3-(Diethylboryl)pyridines

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6829-6834

  Sugihara, Yoshikazu ^a   Takakura, Katsuto ^b   Murafuji, Toshihiro ^a   Miyatake, Ryuta ^b   Nakasuji, Kazuhiro ^b   Kato, Masako ^c   Yano, Shigenobu ^c  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c NARA WOMEN'S UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000923447     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960825k     Document Type: Article

References (31)

1. A preliminary communication has appeared: Sugihara, Y.; Miyatake, R.; Takakura, K.; Yano, S. J. Chem. Soc. Chem. Commun. 1994, 1925.
2. Terashima, M.; Kakimi, H.; Ishikura, M.; Kamata, M.; Chem. Pharm. Bull. 1983, 31, 4573.
3. Ishikura, M.; Kamada, M.; Terashima, M. Heterocycles 1984, 22, 265; Idem. Synthesis 1984, 936. Ishikura, M. Kamada, M.; Ohta, T.; Terashima, M. Heterocycles 1984, 22, 2475.
4. Ishikura, M.; Kamada, M.; Terashima, M. Heterocycles 1984, 22, 265; Idem. Synthesis 1984, 936. Ishikura, M. Kamada, M.; Ohta, T.; Terashima, M. Heterocycles 1984, 22, 2475.
5. Ishikura, M.; Kamada, M.; Terashima, M. Heterocycles 1984, 22, 265; Idem. Synthesis 1984, 936. Ishikura, M. Kamada, M.; Ohta, T.; Terashima, M. Heterocycles 1984, 22, 2475.
6. For the Lewis acidity of the trivalent boron conjugated to the electron-rich aromatic ring, see: Sugihara, Y.; Yagi, T.; Murata, I.; Imamura, A. J. Am. Chem. Soc. 1992, 114, 1479. Sugihara, Y.; Miyatake, R.; Yagi, T.; Murata, I.; Jinguji, M.; Nakazawa, T.; Imamura, A. Tetrahedron 1994, 50, 6495. Sugihara, Y.; Miyatake, R.; Murata, I.; Imamura, A. J. Chem. Soc., Chem. Commun. 1995, 1249.
7. For the Lewis acidity of the trivalent boron conjugated to the electron-rich aromatic ring, see: Sugihara, Y.; Yagi, T.; Murata, I.; Imamura, A. J. Am. Chem. Soc. 1992, 114, 1479. Sugihara, Y.; Miyatake, R.; Yagi, T.; Murata, I.; Jinguji, M.; Nakazawa, T.; Imamura, A. Tetrahedron 1994, 50, 6495. Sugihara, Y.; Miyatake, R.; Murata, I.; Imamura, A. J. Chem. Soc., Chem. Commun. 1995, 1249.
8. For the Lewis acidity of the trivalent boron conjugated to the electron-rich aromatic ring, see: Sugihara, Y.; Yagi, T.; Murata, I.; Imamura, A. J. Am. Chem. Soc. 1992, 114, 1479. Sugihara, Y.; Miyatake, R.; Yagi, T.; Murata, I.; Jinguji, M.; Nakazawa, T.; Imamura, A. Tetrahedron 1994, 50, 6495. Sugihara, Y.; Miyatake, R.; Murata, I.; Imamura, A. J. Chem. Soc., Chem. Commun. 1995, 1249.
9. Garcia, E. E.; Greco, C. V.; Hunsberger, I. M. J. Am. Chem. Soc. 1960, 82, 4430.
10. Comins, D. L.; Killpack, M. O. J. Org. Chem. 1990, 55, 69.
11. Pugmirc, R. J.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 699. Jones, A. J.; Grant, D. M.; Russell, J. G.; Fraenkel, G. J. Phys. Chem. 1969, 73, 1624.
12. Pugmirc, R. J.; Grant, D. M. J. Am. Chem. Soc. 1968, 90, 699. Jones, A. J.; Grant, D. M.; Russell, J. G.; Fraenkel, G. J. Phys. Chem. 1969, 73, 1624.
13. Doty, J. C.; Babb, B.; Grisdale, P. J.; Glogowski, M.; Williams, J. L. R. J. Organomet. Chem. 1972, 38, 229.
14. Nöth, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3089. Spielvogel, W. R. Nutt, R. Izydore, R. A. J. Am. Chem. Soc. 1975, 97, 1609. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Spring-Verlag, New York, 1978.
15. Nöth, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3089. Spielvogel, W. R. Nutt, R. Izydore, R. A. J. Am. Chem. Soc. 1975, 97, 1609. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Spring-Verlag, New York, 1978.
16. Nöth, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3089. Spielvogel, W. R. Nutt, R. Izydore, R. A. J. Am. Chem. Soc. 1975, 97, 1609. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, Spring-Verlag, New York, 1978.
17. Nöth, H.; Wrackmeyer, B. Chem. Ber. 1974, 107, 3070.
18. Nöth, H.; Vahrenkamp, H. Chem. Ber. 1966, 99, 1049.
19. Levy, G. C.; Lichter, R. L. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy; John Willey & Sons, Inc.: New York, 1979.
20. Zettler, F.; Hausen, H. D.; Hess, H. J. Organomet. Chem. 1974, 72, 157.
21. Hughes, E. W. J. Am. Chem. Soc. 1956, 78, 502.
22. Thorne, L. R.; Suenram, R. D. Lovas, F. J. J. Chem. Phys. 1983, 78, 167.
23. Kuznesof, P. M.; Kuczkowski, R. L. Inorg. Chem. 1978, 17, 2308.
24. Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586.
25. Toyota, S.; Oki, M. Bull. Chem. Soc. Jpn. 1992, 65, 1832.
26. Haaland, A. Angew. Chem. Int. Ed. Engl. 1989, 28, 992.
27. Fujita, M.; Ogura, K. J. Synth. Org. Chem. Jpn. 1994, 52, 839. Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079.
28. Fujita, M.; Ogura, K. J. Synth. Org. Chem. Jpn. 1994, 52, 839. Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079.
29. Debaerdemaeker, T.; Germain, G.; Main, P.; Refaat, L. S.; Tate, C.; Woolfson, M. M. Computer programs for the automatic solution of crystal structures from X-ray diffraction data; University of New York, U.K, 1988.
30. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDlF program system, Technical Report of the Crystallography Laboratory; University of Nijmegen: The Netherlands 1992.
31. Gilmore, C. J. MITHRIL-an integrated direct methods computer program; University of Glasgow, Scotland, 1990.