Unique stereochemistry of 3-borabicyclo[3.3.1]nonane derivatives

Russian Chemical Bulletin

Volumn 53, Issue 9, 2004, Pages 1963-1977

  Gurskii, M E ^a   Lyssenko, K A ^b   Karionova, A L ^a   Belyakov, P A ^a   Potapova, T V ^a   Antipin, M Yu ^b   Bubnov, Yu N ^a,b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

3 Borabicyclo 3.3.1 nonane derivatives; Conformational analysis; Dynamic NMR spectroscopy; Quantum chemical calculations; Transannular interactions; X ray diffraction data

Indexed keywords

BICYCLO COMPOUND;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; MATHEMATICAL MODEL; MOLECULAR INTERACTION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; QUANTUM CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY DIFFRACTION;

EID: 21344435269     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-005-0057-2     Document Type: Article

References (48)

1. N. S. Zefirov and V. A. Palyulin, in Topics in Stereochemistry, Eds E. L. Eliel and S. H. Wilen, Wiley, New York, 1991, 20, 171-230.
2. (a) V. S. Mastryukov, E. L. Osina, O. V. Dorofeeva, M. V. Popik, L. V. Vilkov, and N. A. Belikova, J. Mol. Structure, 1979, 52, 211;
3. (b) V. S. Mastryukov, M. V. Popik, O. V. Dorofeeva, A. V. Golubinskii, L. V. Vilkov, N. A. Belikova, and N. L. Allinger, J. Am. Chem. Soc., 1981, 103, 1334.
4. J. A. Peters, Synthesis, 1979, 321.
5. T. Sasaki, Adv. Heterocycl. Chem., 1982, 30, 79.
6. B. M. Mikhailov and Yu. N. Bubnov, Organoboron Compounds in Organic Synthesis, Harwood Acad. Sci. Publ., London - New York, 1984.
7. R. S. Fort, Adamantane, The Chemistry of Diamond Molecules, Decker, New York-Basel, 1976.
8. T. A. Henry, Plant Alkaloids, J. and A. Churdull Ltd, London, 1956.
9. N. K. Hurt, S. R. Jones, and J. A. Lamberton, Aust. J. Chem., 1967, 20, 561.
10. S. W. Pelletier, Chemistry of the Alkaloids, van Nostrand, New York, 1970.
11. J. A. Peters, J. M. van der Toorn, and H. van Bekkum, Tetrahedron, 1977, 33, 349.
12. Y. Senda, J. I. Ishiyama, and S. Imaizumi, J. Chem. Soc., Perkin Trans. 2, 1981, 90.
13. H.-J. Schneider and W. Ansorge, Tetrahedron, 1977, 33, 265.
14. J. A. Peters, P. E. J. Peters van Granenburgh, J. M. van der Toorn, Th. M. Wortel, and H. van Bekkum, Tetrahedron, 1978, 34, 2217.
15. Th. R. Bok and W. N. Speckamp, Tetrahedron, 1979, 35, 267.
16. J. F. Richardson and T. S. Sorensen, Can. J. Chem., 1985, 63, 1166.
17. M. E. Gurskii, A. S. Shashkov, and B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 341
18. [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981, 30 (Engl. Transl.)].
19. M. E. Gurskii, A. S. Shashkov, and B. M. Mikhailov, J. Organomet. Chem., 1980, 199, 171.
20. M. E. Gurskii, I. D. Gridnev, Yu. N. Bubnov, A. Pelter, and P. Rademacher, J. Organomet. Chem., 1999, 590, 2.
21. M. E. Gurskii, A. V. Gueiderikh, Yu. N. Bubnov, M. Yu. Antipin, K. A. Lyssenko, I. D. Gridnev, R. Boese, and D. Blaeser, J. Organomet. Chem., 2001, 636, 3.
22. K. A. Lyssenko, M. Yu. Antipin, M. E. Gurskii, Yu. N. Bubnov, A. L. Karionova, and R. Boese, Chem. Phys. Lett., 2004, 384, 40.
23. N. S. Zefirov, Usp. Khim., 1975, 44, 413
24. [Russ. Chem. Rev., 1975, 44, 196 (Engl. Transl.)].
25. J. A. Peters, J. H. van der Toorn, and H. van Bekkum, Tetrahedron, 1977, 33, 349.
26. (a) R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendron Press, Oxford, 1990;
27. (b) R. F. W. Bader, J. Chem. Phys., 1998, A102, 7314.
28. K. R. Leopold, M. Canagaratna, and J. A. Philips, Acc. Chem. Res., 1997, 30, 57.
29. A. A. Korlyukov, K. A. Lyssenko, M. Yu. Antipin, V. N. Kirin, E. A. Chernyshev, and S. P. Knyazev, Inorg. Chem., 2002, 41, 5043.
30. E. Espinosa, E. Mollins, and C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.
31. K. A. Lyssenko and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 2001, 400
32. [Russ. Chem. Bull., Int. Ed., 2001, 50, 418].
33. C. Gatti, E. May, and F. Cargnoni, J. Phys. Chem., 2002, A106, 2707.
34. R. Boese, N. Niederprüm, and D. Bläser, in Molecules in Natural Science and Medicine: An Encomium for Linus Pauling, Eds Z. Maksić and M. Eckert-Maksić, Ellis Horwood Limited, England, 1991, 103.
35. B. M. Mikhailov, M. E. Gurskii, S. V. Baranin, Yu. N. Bubnov, M. V. Sergeeva, K. A. Potekhina, A. V. Maleev, and Yu. T. Struchkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1645
36. [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 1494 (Engl. Transl.)].
37. N. S. Zefirov, V. S. Blagoveshchensky, I. Y. Kazimirchik, and N. S. Surova, Tetrahedron, 1971, 27, 3111.
38. M. Oki, Application of Dynamic NMR Spectroscopy to Organic Chemistry, in Methods in Stereochemichal Analysis, Ed. A. P. Marchand, VCH Publishers, Inc., 1985, 4, p. 96.
39. H. Beall and C. H. Bushweller, Chem. Rev., 1973, 73, 465.
40. C. L. Perrin and T. J. Dwyer, Chem. Rev., 1990, 90, 935.
41. Yu. N. Bubnov, M. E. Gursky, I. D. Gridnev, A. V. Ignatenko, Yu. A. Ustynyuk, and V. I. Mstislavsky, J. Organomet. Chem., 1992, 424, 127.
42. N. M. D. Brown, F. Davidson, and J. W. Wilson, J. Organomet. Chem., 1981, 209, 1.
43. B. M. Mikhailov and K. L. Cherkasova, Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 1244
44. [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 20, 1150 (Engl. Transl.)].
45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Revision A. 7, Gaussian, Inc., Pittsburgh (PA), 1998.
46. J. Cheeseman, T. A. Keith, and R. W. F. Bader, AIMPAC Program Package, McMaster University, Hamilton (Ontario), 1992.
47. A. V. Shastin, T. I. Godovikova, S. P. Golova, M. V. Povorin, D. E. Dmitriev, M. O. Dekaprilevich, Yu. A. Strelenko, Yu. T. Struchkov, L. I. Khmel'nitskii, and B. L. Korsunskii, Khim. Geterotsikl. Soedin., 1995, 31, 679
48. [Chem. Heterocycl. Compd., 1995, 31 (Engl. Transl.)].