Hydroboration of bis(trimethylsilyl)ethyne. New aspects of hydroboration

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 58, Issue 2-3, 2003, Pages 133-138

  Wrackmeyer, Bernd ^a   Tok, O L ^a   Milius, Wolfgang ^a   Bhatti, Moazzam H ^a,b   Ali, Saqib ^a,b  

^a UNIVERSITY OF BAYREUTH   (Germany)

^b QUAID I AZAM UNIVERSITY   (Pakistan)

Author keywords

Alkenes; Alkynes; Allenes

Indexed keywords

ACETYLENE; ENERGY DISPERSIVE X RAY ANALYSIS; IRRADIATION; SILICON; X RAY DIFFRACTION ANALYSIS;

ALKYNES; ALLENES; ANALOGOUS STRUCTURES; DELOCALISATION; HYDROBORATION; SOLID-STATE STRUCTURES; TRIMETHYLSILYL; WITHOUT UV IRRADIATIONS;

OLEFINS;

1,1,4,4 TETRAKIS(TRIMETHYLSILYL) 4 [9 (BORABICYCLO[3.3.1]NONYL)]BUTA 1,2 DIENE; ACETYLENE DERIVATIVE; ALLENE DERIVATIVE; BIS(TRIMETHYLSILYL)ETHYNE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CRYSTALLIZATION; HEATING; HYDROBORATION; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STRUCTURE ANALYSIS; ULTRAVIOLET IRRADIATION; X RAY ANALYSIS;

EID: 0038074140     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2003-0119     Document Type: Article

References (45)

1. J. A. Soderquist, J. C. Colberg, L. DelValle, J. Am. Chem. Soc. 111, 4873 (1989).
2. a) K. Uchida, K. Utimoto, H. Nozaki, J. Org. Chem. 41, 2941 (1976);
3. b) K. Uchida, K. Utimoto, H. Nozaki, Tetrahedron 33, 2987 (1977);
4. c) G. Zweifel, S. J. Backlund, J. Am. Chem. Soc. 99, 3184 (1977);
5. d) M. Hoshi, Y. Masuda, A. Arase, Bull. Chem. Soc. Jpn. 66, 914 (1993).
6. a) S. Rajogopalan, G. Zweifel, Synthesis 113 (1984);
7. b) J. A. Miller, G. Zweifel, Synthesis 288 (1981);
8. c) J. A. Miller, G. Zweifel, J. Am. Chem. Soc. 103, 6217 (1981);
9. d) J. A. Soderquist, G. Leon. Tetrahedron Lett. 39, 3989 (1998);
10. e) D. A. Singleton, J. P. Martinez, Tetrahedron Lett. 32, 7365 (1991).
11. a) R. Köster, G. Seidel, B. Wrackmeyer, Angew. Chem. 106, 2380 (1994); Angew. Chem. Int. Ed. 33, 2294 (1994);
12. a) R. Köster, G. Seidel, B. Wrackmeyer, Angew. Chem. 106, 2380 (1994); Angew. Chem. Int. Ed. 33, 2294 (1994);
13. b) R. Köster, G. Seidel, R. Boese, B. Wrackmeyer, Z. Naturforsch. 50b. 439 (1995);
14. c) B. Wrackmeyer H.-J. Schanz, Coll. Czech. Chem. Commun. 62, 1254 (1997).
15. N. S. Hosmane, N. N. Sirmokadam, M. N. Mollenhauer, J. Organomet. Chem. 279, 359 (1985).
16. B. Wrackmeyer, Polyhedron 5, 1709 (1986).
17. 3B and various other ethyldiboranes(6): R. Köster, G. Bruno, P. Binger, Liebigs Ann. Chem. 644, 1 (1961).
18. R. Köster, G. Seidel, F. Lutz, C. Krüger, G. Kehr, B. Wrackmeyer, Chem. Ber. 127, 813 (1994).
19. A. Hassner, J. A. Soderquist, J. Organomet. Chem. 131, C1 (1977).
20. H. Binder, W. Ehmann, K. Dementzis, Z. Naturforsch. 46b, 581 (1991).
21. R. L. Ernest, W. Quintana, R. Rosen, P. J. Carroll, L. G. Sneddon, Organometallics 6, 80 (1987).
22. F. Meyer, M. U. Schmidt, P. Paetzold, Chem. Ber. 128, 947 (1995).
23. a) B. Wrackmeyer, C. Bihlmayer, J. Chem. Soc. Chem. Commun. 1093 (1981);
24. b) B. Wrackmeyer, J. Organomet. Chem. 205, 1 (1981);
25. c) B. Wrackmeyer, R. Zentgraf, J. Chem. Soc. Chem. Commun. 402 (1978).
26. B. Wrackmeyer, C. Bihlmayer, M. Schilling, Chem. Ber. 116, 3182 (1983).
27. B. Wrackmeyer, U. Dörfler, G. Kehr, H. E. Maisel, W. Milius, J. Organomet. Chem. 524, 169 (1996).
28. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
29. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
30. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
31. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
32. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
33. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
34. Hyperconjugative stabilising effects are well documented for silyl, germyl and stannyl groups in β-positions: a) J. B. Lambert, Y. Zhao, H. Wu, J. Org. Chem. 64, 2729 (1999); b) V. G. Lakhtin, V. D. Sheludyakov, V. M. Nosova, A. V. Kisin, E. A. Chermyshev, Dok. Akad. Nauk 377, 55 (2001); c) V. Gabelica, A. J. Kresge, J. Am. Chem. Soc. 118, 3838 (1996): d) Y. Apeloig, R. Biton, A. Abu-Freih, J. Am. Chem. Soc. 115, 2522 (1993); e) H.-U. Siehl, F. P. Kaufmann, J. Am. Chem. Soc. 114, 4937 (1992); f) A. Berndt. Angew. Chem. 105, 1034 (1993); Angew. Chem. Int. Ed. Engl. 32, 985 (1993).
35. B. Wrackmeyer, Coord. Chem. Rev. 145, 125 (1995).
36. B. Wrackmeyer, S. Kerschl, U. Klaus, Z. Naturforsch. 57b, ??? (2002).
37. B. Wrackmeyer, in R. B. King, J. J. Eisch (eds.): Organometallic Syntheses, Vol. 4, pp. 559-560, Elsevier, New York (1988).
38. a) G. A. Morris, R. Freeman, J. Am. Chem. Soc. 101, 760 (1979);
39. b) G. A. Morris, J. Am. Chem. Soc. 102, 428 (1980);
40. c) G. A. Morris, J. Magn. Reson. 41, 185 (1980);
41. d) D. P. Burumn, R. R. Ernst, J. Magn. Reson. 39, 163 (1980).
42. E. Kupče, E. Lukevics, in E. Buncel, J. R. Jones (eds.): Isotopes in the Physical and Biomedical Science, Vol. 2, pp. 213-295, Elsevier, Amsterdam (1991).
43. B. Wrackmeyer, G. Seidel, R. Köster, Magn. Reson. Chem. 38, 520 (2000).
44. B. Wrackmeyer, W. Milius, E. V. Klimkina, Yu, N. Bubnov, Chem. Eur. J. 7, 775 (2001).
45. B. Wrackmeyer, O. L. Tok, Magn. Reson. Chem. 40, 406 (2002).