Studies on the synthesis of borazines from borane and 1,2-aminoalcohols

Tetrahedron Letters

Volumn 47, Issue 43, 2006, Pages 7603-7606

  Stepanenko, Viatcheslav ^a   Ortiz Marciales, Margarita ^a   Barnes, Charles E ^b   Garcia, Carmelo ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AMINOPHENOL DERIVATIVE; BORANE DERIVATIVE; BORON DERIVATIVE; METHYL GROUP; NOREPHEDRINE; OXAZABOROLIDINE DERIVATIVE; PHENYL GROUP;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; PHYSICAL CHEMISTRY; POLYMERIZATION; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

EID: 33748748368     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.071     Document Type: Article

References (44)

1. For reviews see:. Glushkov V.A., and Tolstikov A.G. Russ. Chem. Rev. 73 (2004) 581-608
2. Corey E.J. Angew. Chem., Int. Ed. 41 (2002) 1650-1667
3. Fache F., Schulz E., Tomamasino M., and Lemaire M. Chem. Rev. 100 (2000) 2159-2231
4. Corey E.J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986-2012
5. Deloux L., and Srebik M. Chem. Rev. 93 (1993) 763-784
6. Singh V.K. Synthesis (1992) 605-617
7. For representative examples see:. Joshi N.N., Srebnik M., and Brown H.C. Tetrahedron Lett. 30 (1989) 5551-5554
8. Ryu D.H., and Corey E.J. J. Am. Chem. Soc. 126 (2004) 8106-8107
9. Takasu M., and Yamomoto H. Synlett (1990) 194-197
10. Sartor D., Saffrich J., and Helmchen G. Synlett (1990) 197-199
11. Corey E.J., Shibata T., and Lee T.W. J. Am. Chem. Soc. 124 (2002) 3808-3809
12. Berkessel A., Mukherjee S., and Lex J. Synlett (2006) 41-44
13. Kinugasa M., Harada T., and Oku A. Tetrahedron Lett. 39 (1998) 4529-4532
14. Kinugasa M., Harada T., and Oku A. Tetrahedron Lett. 39 (1998) 5535-5536
15. Bringmann G., and Hartung T. Angew. Chem., Int. Ed. Engl. 31 (1992) 761
16. Kiyooka S., Kaneko Y., Komura M., Matsuo H., and Nakano M. J. Org. Chem. 65 (1991) 2276-2278
17. Itsuno S., Nakano M., Miyazaki K., Masuda H., and Ito K. J. Chem. Soc., Perkin Trans. 1 (1885) 2039-2044
18. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
19. Itsuno S., Sakurai Y., Shimizu K., and Ito K. J. Chem. Soc., Perkin Trans. 1 (1990) 1859-1863
20. Cho B.T., and Ryu M.h. Bull. Korean Chem. Soc. 15 (1994) 191
21. Quallich G.J., Keavey K.N., and Woodall T.M. Tetrahedron Lett. 36 (1995) 4729-4732
22. Yadav J.S., Reddy P.T., and Hashim S.R. Synlett 7 (2000) 1049-1051
23. Fontaine E., Namane C., Meneyrol J., Geslin M., Serva L., Royssey E., Tissandie S., Maftouh M., and Roger P. Tetrahedron: Asymmetry 12 (2001) 2185-2189
24. Krzeminski M.P., and Zaildewiccz M. Tetrahedron: Asymmetry 14 (2003) 1463-1466
25. Brown J.M., and Lloyd-Jones G.C. Tetrahedron: Asymmetry 1 (1990) 865-868
26. Quallich, G. J. U.S. Patent 6037505, 2000.
27. Ortiz-Marciales M., González E., Figueroa R., De Jesús M., Martínez J., Espinosa S., and Correa W. Organic Lett. 5 (2003) 3447-3449
28. Brown J.M., Guy C., Lloyd-Jones G.C., and Layzell T.P. Tetrahedron: Asymmetry 4 (1993) 2151-2154
29. Lang A., Noth H., and Schmidt M. Chem. Ber. 130 (1997) 241-246
30. Mathre D.J., Thompson A.S., Douglas A.W., Carroll J.D., Corley E.G., and Grabowski E.J.J. J. Org. Chem. 58 (1993) 2880-2888
31. Ortiz-Marciales M., De Jesus M., Gonzales E., Raptis R.G., and Baran P. Acta Crystallogr., Sect. C 60 (2004) 173-175
32. Tlahuext H., Santiesteban F., García-Báez E., and Contreras R. Tetrahedron: Asymmetry 5 (1994) 1579-1588
33. Santiesteban F., Mancilla T., Klaébe A., and Contreras R. Tetrahedron Lett. 24 (1983) 759-760
34. Brunel J.M., Maffei M., and Buono G. Tetrahedron: Asymmetry 4 (1993) 2255-2260
35. The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the Deposition Number CCDC 288342.
36. Niedenzu K., and Dawson K.J. Boron-Nitrogen Compounds (1965), Academic Press, New York
37. Ryschkewictsch G.E., and Willings J.W. Inorg. Chem. 9 (1970) 314
38. Jaska C.A., Temple K., Lough A.J., and Manners I. J. Am. Chem. Soc. 125 (2003) 9424-9434
39. Rudner, B.; Harris, J. J. U.S. Patent 3 100 791, 1959.
40. Brotherton R.J., and Steinberg H.J. J. Org. Chem. 26 (1961) 4632-4634
41. Harris J.J., and Rudner B. J. Org. Chem. 27 (1962) 3848-3851
42. Cragg R.H., and Weston A.F. J. Chem. Soc., Chem. Commun. (1972) 79-80
43. Cragg R.H., and Weston A.F. J. Chem. Soc., Dalton Trans. (1975) 93-95
44. Cragg R.H., and Weston A.F. J. Chem. Soc., Dalton Trans. (1975) 1761-1764