Reactions of prolinol with borane-tetrahydrofuran: Anomalous dimerization of a 1,3,2-oxazaborolidine

Chemische Berichte

Volumn 130, Issue 2, 1997, Pages 241-246

  Lang, Andreas ^a   Nöth, Heinrich ^a   Schmidt, Martin ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

(2 Pyrroiidinylmethoxo)borane, anomalous dimer; 5 Phenyl 3,4 dimethyl 1,3,2 oxazaborolidine, anomalous dimer; Boron compounds; Reaction intermediates

Indexed keywords

EID: 0013547029     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300217     Document Type: Article

References (28)

1. [Part 233: S. Grundei, H. Nöth, R. T. Paine, Chem. Ber. 1996, 729, 1233-1241.
2. See Gmelin, Handbuch der Anorganischen Chemie, 8th ed., vol. 2, 4th supplement, 1993.
3. See Gmelin, Handbuch der Anorganischen Chemie, 8th ed., vol. 3b, 4th Supplement, 1992.
4. For example, compounds of type 1 will not add oxidatively to Pt(0) or Pd(0) with formation of transition-metal-boron bonds. R. Schur, Dipl. Thesis, University of Munich, 1996.
5. J. M. Brown, G. C. Lloyd-Jones, Tetrahedron Asymm. 1990, 1, 869-872.
6. N. N. Jostin, M. Slzenik, H. C. Brown, Tetrahedron Lett. 1989, 30, 5551-5552.
7. V. K. Singh, Synthesis 1992, 605-617;
8. B. B. Lohray, V. Bushan, Angew. Chem. 1992, 104, 740-783;
9. Angew. Chem. Int. Ed. (Engl.) 1992, 31, 715.
10. E. J. Corey, J. O. Link, R. K. Bakshi, Tetrahedron Lett. 1992, 33, 7107-7110.
11. H. Nöth, S. Weber, B. Rasthofer, C. K. Narula, A. Konstantinov, J. Pure Appl. Chem. 1983, 55, 1453-1462.
12. - H. Nöth, B. Rasthofer, S. Weber, Z. Naturforsch. Part B 1984, 39, 1058.
13. P. Kölle, H. Nöth, Chem. Ber. 1986, 119, 313.
14. - H. Nöth, B. Rasthofer, ibid. 1986, 119, 2075.
15. D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933-2960.
16. J. Bielawsky, K. Niedenzu, Synth. React. Inorg. Metal-Org. Chem. 1980, 10, 479-489.
17. - H. Fußstetter, H. Nöth, W. Winterstein, Chem. Ber. 1977, 770, 1931-1938.
18. H. G. Köhn, A. Meiler, Z. Naturforsch., Part B 1980, 35, 447-453.
19. H. Nöth, B. Wrackmeyer, NMR Spectroscopy of Boron Compounds, vol. 14 of the series N MR -Basic Principles and Progress (Eds.: P. Diehl, E. Fluck, R. Kosfeld), Springer Publishers, Heidelberg-Berlin-New York, 1973.
20. J. Karplus, J. Chem. Soc. 1959, 30, 11;
21. J. Org. Chem. 1963, 85, 2870-2891.
22. From the molecular structure of 9 in the solid state, the following four dihedral angles were determined: H1-C-O-B = 144.7 and 156.7°; Hl'-C-O-B = 96.7 and 84.4°.
23. P. Paetzold, Advances in Inorganic and Radiochemistry, 1987, 31, 123-170.
24. 2B bridge in the IR spectra, they suggested that the dimer contains an intermolecular B-O coordination as shown by formula 10b.
25. H. Nöth, unpublished observations.
26. 4 salts. S. G. Shore, R. W. Parry, J. Am. Chem. Soc. 1955, 77, 1-12.
27. - S. G. Shore, D. Cowley, ibid. 1965, 87, 2755-2756.
28. SHELXT, Siemens Analytical Instruments, Version 5.1, 1994; SHELX 93, G. W. Sheldrick, University of Göttingen.