Synthesis of heteronuclear bifunctional Lewis acids by transmetalation of 1,8-bis(trimethylstannyl)naphthalene with BCl3

Canadian Journal of Chemistry

Volumn 80, Issue 10, 2002, Pages 1308-1312

  Schulte, Marcus ^a   Gabbaï, François P ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Multidentate Lewis acids; Organoboranes; Organostannanes

Indexed keywords

BORON COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY ANALYSIS;

LEWIS ACIDS;

NAPHTHALENE; AROMATIC COMPOUNDS;

1 (DICHLOROMETHYLSTANNYL) 8 (CHLOROMETHYLBORYL)NAPHTHALENE; 1 (DICHLOROMETHYLSTANNYL) 8 (DICHLOROBORYL)NAPHTHALENE; 1 (DICHLOROMETHYLSTANNYL) 8 (HYDROXYMETHYLBORYL)NAPHTHALENE; 1,8 BIS(TRIMETHYLSTANNYL)NAPHTHALENE; LEWIS ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; WARMING; X RAY CRYSTALLOGRAPHY;

ZOOLOGY;

EID: 0036925693     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v02-177     Document Type: Article

References (41)

1. (a) H. Nöth and H. Vahrenkamp. J. Organomet. Chem. 11, 399 (1968);
2. (b) H. Nöth and P. Fritz. Z. Anorg. Allg. Chem. 322, 297 (1963);
3. (c) J.E. Burch, W. Gerrard, M. Howarth, and E.F. Mooney. J. Chem. Soc. 4916 (1960).
4. F. Jäkle, A.J. Lough, and I. Manners. Chem. Commun. 453 (1999).
5. D. Kaufmann. Chem. Ber. 120, 901 (1987).
6. J.J. Eisch and B.W. Kotowicz. Eur. J. Inorg. Chem. 761 (1998).
7. M.V. Metz, D.J. Schwartz, C.L. Stern, P.N. Nickias, and T.J. Marks. Angew. Chem. Int. Ed. Engl. 39, 1312 (2000).
8. M. Fontani, F. Peters, W. Scherer, W. Wachter, M. Wagner, and P. Zanello. Eur. J. Inorg. Chem. 1453 (1998).
9. (a) D.F. Schriver and M.J. Biallas. J. Am. Chem. Soc. 89, 1078 (1967);
10. (b) D.J. Saturnino, M. Yamauchi, W.R. Clayton, R.W. Nelson, and S.G. Shore. J. Am. Chem. Soc. 97, 6063 (1975).
11. (a) H.E. Katz. J. Org. Chem. 50, 5027 (1985);
12. (b) H.E. Katz. Organometallics, 6, 1134 (1987).
13. M. Reilly and T. Oh. Tetrahedron Lett. 35, 217 (1995).
14. H.E. Katz. J. Org. Chem. 54, 2179 (1989).
15. (a) K. Nozaki, M. Yoshida, and H. Takaya. Bull. Chem. Soc. Jpn. 69, 2043 (1996);
16. (b) K. Nozaki, T. Tsutsumi, and H. Takaya. J. Org. Chem. 60, 6668 (1995).
17. E.Y.-X. Chen and T.J. Marks. Chem. Rev. 100, 1391 (2000).
18. (a) V.C. Williams, W.E. Piers, W. Clegg, M.R.J. Elsegood, S. Collins, and T.B. Marder. J. Am. Chem. Soc. 121, 3244 (1999);
19. (b) V.C. Williams, C. Dai, Z. Li, S. Collins, W.E. Piers, W. Clegg, M.R.J. Elsegood, and T.B. Marder. Angew. Chem. Int. Ed. Engl. 38, 3695 (1999);
20. (c) W.E. Piers, G.J. Irvine, and V.C. Williams. Eur. J. Inorg. Chem. 2131 (2000);
21. (d) V.C. Williams, G.J. Irvine, W.E. Piers, Z. Li, S. Collins, W. Clegg, M.R.J. Elsegood, and T.B. Marder. Organometallics, 19, 1619 (2000);
22. (e) L.D. Henderson, W.E. Piers, G.J. Irvine, and R. McDonald. Organometallics, 21, 340 (2002).
23. M. Reiley and T. Oh. Tetrahedron Lett. 36, 221 (1995).
24. B. Schilling, V. Kaiser, and D. Kaufmann. Chem. Ber. 130, 923 (1997).
25. D. Seyferth and S.C. Vick. J. Organomet. Chem. 141, 173 (1977).
26. J.D. Hoefelmeyer, M. Schulte, and F.P. Gabbaï. Inorg. Chem. 40, 3833 (2001).
27. (a) M. Tschinkl, J.D. Hoefelmeyer, T.M. Cocker, R.E. Bachman, and F.P. Gabbaï. Organometallics, 19, 1826 (2000);
28. (b) J.D. Hoefelmeyer, D. Brode, and F.P. Gabbaï. Organometallics, 20, 5653 (2001).
29. M. Schulte and F.P. Gabbaï. Chem. Eur. J. 8, 3802 (2002).
30. (a) J.D. Hoefelmeyer and F.P. Gabbaï. J. Am. Chem. Soc. 122, 9054 (2000);
31. (b) J.D. Hoefelmeyer and F.P. Gabbaï. Organometallics, 21, 982 (2002).
32. A. Hergel, H. Pritzkow, and W. Siebert. Angew. Chem. Int. Ed. Engl. 33, 1247 (1994).
33. J.A. Gamboa, A. Sundararaman, L. Kakalis, A.J. Lough, and F. Jäkle. Organometallics, 21, 4169 (2002).
34. R. Altmann, K. Jurkschat, M. Schürmann, D. Dakternieks, and A. Duthie. Organometallics, 17, 5858 (1998).
35. A.G. Davies. Organotin Chemistry. VCH, Weinheim. 1997. Chap 2.
36. U. Kolb, M. Beuter, and M. Dräger, Inorg. Chem. 33, 4522 (1994).
37. (a) J.F. Blount, F. Cozzi, J.R. Damewood Jr, L.D. Iroff, U. Sjostrand, and K. Mislow. J. Am. Chem. Soc. 102, 99 (1980);
38. (b) R. Schröck, K. Angermaier, A. Sladek, and H. Schmidbaur. Organometallics, 13, 3399 (1994).
39. G. Sheldrick. 1986. SHELXS-86 Program for Crystal Structure Solution [Computer Program]. Institut für Anorganische Chemie, Universität Göttingen. Göttingen, Germany.
40. G. Sheldrick. 1997. SHELXL-97 Program for Crystal Structure Refinement [Computer Program]. Institut für Anorganische Chemie, Universität, Göttingen. Göttingen, Germany.
41. M. Schulte, M. Schürmann, and K. Jurkschat. Chem. Eur. J. 7, 347 (2001), and refs. cited therein.