Selenium- and tellurium-bridged overcrowded homomerous bistricyclic aromatic enes

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 2000, Pages 725-735

  Levy, Amalia ^a   Biedermann, P Ulrich ^a   Cohen, Shmuel ^a   Agranat, Israel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; BENZENE; CALCULATIONS; CONFORMATIONS; DIMERIZATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SELENIUM; STABILITY; TELLURIUM; X RAY ANALYSIS;

ANTI FOLDED CONFORMATIONS; OVERCROWDED HOMOMEROUS BISTRICYCLIC AROMATIC ENES; SELENIUM BRIDGE; TELLURIUM BRIDGE;

AROMATIC COMPOUNDS;

EID: 0034175138     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908715j     Document Type: Article

References (66)

1. G. Shoham, S. Cohen, R. M. Suissa and I. Agranat, in Molecular Structure Chemical Reactivity and Biological Activity, eds. J. J. Stezowski, J.-L. Huang and M.-C. Shao, Oxford University Press, Oxford, 1988, p. 290.
2. J. Sandström, in The Chemistry of Double-Bonded Functional Groups, Supplement A3, ed. S. Patai, Wiley, New York 1997, p. 1253.
3. P. U. Biedermann, J. J. Stezowski and I. Agranat, in Advances in Theoretically Interesting Molecules, vol. 4, ed. R. P. Thummel, JAI Press, Stamford, CN, 1998, p. 245.
4. P. U. Biedermann, A. Levy, J. J. Stezowski and I. Agranat, Chirality, 1995, 7, 199.
5. A. Z.-Q. Khan and J. Sandström, J. Am. Chem. Soc., 1988, 110, 4843.
6. N. A. Bailey and S. E. Hull, Acta Crystalogr., Sect. B, 1978, 34, 3289.
7. J.-S. Lee and S. C. Nyburg, Acta Crystallogr., Sect. C, 1985, 41, 560.
8. J. F. D. Mills and S. C. Nyburg, J. Chem. Soc., 1963, 308.
9. Y. Tapuhi, M. R. Suissa, S. Cohen, P. U. Biedermann, A. Levy and I. Agranat, J. Chem. Soc., Perkin Trans. 2, 2000, 93.
10. K. S. Dichmann, S. C. Nyburg, F. H. Pickard and J. A. Potworowski, Acta Crystallogr., Sect. B, 1974, 30, 27.
11. W. I. Smid, A. M. Schoevaars, W. Kruizinga, N. Veldman, W. J. J. Smeets, A. L. Spek and B. L. Feringa, Chem. Commun., 1996, 2265.
12. I. Agranat and Y. Tapuhi, J. Am. Chem. Soc., 1996, 665.
13. B. L. Feringa, W. F. Jager and B. de Lange, Tetrahedron Lett., 1992, 33, 2887.
14. B. L. Feringa, A. M. Schoevaars, W. F. Jager, B. de Lange and N. P. M. Huck, Enantiomer, 1996, 1, 325.
15. J. F. D. Mills and S. C. Nyburg, J. Chem. Soc., 1963, 927.
16. I. L. Karle and J. Karle, in Organic Selenium Compounds: Their Chemistry and Biology, eds. L. D. Klayman and W. H. H. Günther, Interscience, 1973, p. 989.
17. L. Pauling, The Nature of the Chemical Bond, 3rd edn., Cornell University Press, Ithaca, NY, 1960, p. 93.
18. R. Lesser and R. Weiß, Ber. Dtsch. Chem. Ges., 1914, 47, 2510.
19. K. Šindelàr, E. Svátek, J. Metyšov̀, J. Metys and M. Protiva, Collect. Czech. Chem. Commun., 1969, 34, 3792.
20. (a) I. D. Sadekov and V. I. Minkin, Adv. Heterocycl. Chem., 1995, 63, 1
21. (b) I. D. Sadekov, V. I. Minkin and A. D. Garnovskii, Sulphur Rep., 1985, 4, 63.
22. I. D. Sadekov, A. A. Ladatko and V. I. Minkin, Khim. Geterotsikl. Soedin., 1980, 1342.
23. K. J. Igolin, in Methods of Organic Chemistry (Houben-Weyl), vol. E12b, Organotellurium compounds, ed. D. Klamann, Georg Thieme Verlag, Stuttgart, 1990, pp. 830-840.
24. M. Renson, in The Chemistry of Organic Selenium and Tellurium Compounds, eds. S. Patai and Z. Rappoport, vol. 1, Wiley, Chichester, 1986, p. 399.
25. A. Alberti, F. P. Colonna, M. Guerra, B. F. Bonini, G. Mazzanti, Z. Dinya and G. F. Pedulli, J. Organomet. Chem., 1981, 221, 47.
26. S. Scheibye, R. Shabana and S.-O. Lawesson, Tetrahedron, 1982, 38, 993.
27. M. P. Cava and M. I. Levinson, Tetrahedron, 1985, 41, 5061.
28. B. S. Pedersen, S. Scheibye, N. H. Nilsson and S.-O. Lawesson, Bull. Soc. Chim. Belg., 1978, 87, 223.
29. T. Mukaiyama, T. Sato and J. Hanna, Chem. Lett., 1973, 1041.
30. D. Lenoir and P. Lemmen, Chem. Ber., 1980, 113, 3112.
31. I. Agranat, S. Cohen, J. Isaksson, J. Sandströo and M. R. Suissa, J. Org. Chem., 1990, 55, 4943.
32. J. March, Advanced Organic Chemistry Reaction Mechanism and Structure, 4th edn., Wiley, New York, 1992, p. 1227.
33. M. Hori, T. Kataoka and C.-F. Hsü, Chem. Pharm. Bull., 1974, 22, 15.
34. T. Kataoka, H. Shimizu, K. Tomimatsu, K. Tanaka, M. Hori and M. Kido, Chem. Pharm. Bull., 1990, 38, 874.
35. K. Sh. Karaev, N. G. Furmanova, N. V. Belov, I. D. Sadekov, A. A. Ladatko and V. I. Minkin, Zh. Strukt. Khim., 1981, 22, 106.
36. A. Schönberg, O. Schütz and S. Nickel, Ber. Dtsch. Chem. Ges., 1928, 61B, 1375.
37. A. Schönberg and W. Asker, Chem. Rev., 1945, 37, 1.
38. F. Mayer, Ber. Dtsch. Chem. Ges., 1909, 42, 1132.
39. W. F. Jager, B. de Lange, A. M. Schoevaars, F. van Bolhuis and B. L. Feringa, Tetrahedron: Asymmetry, 1993, 4, 1481.
40. W. R. Blackmore and S. C. Abrahams, Acta Crystallogr., 1955, 8, 323.
41. H. Chen, T. A. Hamor, K. Singh and W. R. McWhinnie, Acta Crystallogr., Sect. C, 1996, 52, 711.
42. J. Farran, A. Alvarez-Larena, J. F. Piniella, M. V. Capparelli and L. Torres-Castellanos, Acta Crystallogr., Sect. C, 1997, 53, 342.
43. Y. V. Zefirov, Crystallogr. Rep. 1997, 42, 111.
44. A. Levy, P. U. Biedermann, S. Cohen and I. Agranat, Phosphorus Sulfur Silicon Relat. Elem., 1998, 136-138, 139.
45. A. Bondi, J. Phys. Chem., 1964, 68, 441.
46. M. Rabinovitz, I. Agranat and E. D. Bergmann, Tetrahedron. Lett., 1965, 1265.
47. N. S. Mills, E. E. Burns, J. G. Hodges, J. Gibbs, E. Esparsa, J. L. Malandra and J. Koch, J. Org. Chem., 1998, 63, 3017.
48. E. D. Bergmann, M. Rabinovitz and I. Agranat, Chem. Commun., 1968, 334.
49. A. Schönberg, U. Sodtke and K. Praefcke Tetrahedron Lett., 1968, 3253
50. A. Schönberg, U. Sodtke and K. Praefcke Chem. Ber., 1969, 102, 1453.
51. I. Agranat and M. R. Suissa, Struct. Chem., 1993, 4, 59.
52. N. H. Martin, N. W. Allen III, K. D. Moore and L. Vo, J. Mol. Struct. (THEOCHEM), 1998, 454, 161.
53. G. Llabrès, M. Baiwir, L. Christiaens and J.-L. Piette, Can. J. Chem., 1979, 57, 2967.
54. S. Gronowitz, A. Konar and A.-B. Hörnfeldt, Org. Magn. Reson., 1977, 9, 213.
55. N. P. Luthra and J. D. Odom, in The Chemistry of Organic Selenium and Tellurium Compounds, eds. S. Patai and Z. Rappoport, vol. 1, Wiley, Chichester, 1986, p. 189.
56. M. Baiwir, G. Llabrès, L. Christiaens, M. Evers and J.-L. Piette, Magn. Reson. Chem., 1987, 25, 129.
57. J. J. P. Stewart, MOPAC 6.00, QCPE 455, 1990.
58. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209
59. J. J. P. Stewart, J. Comput. Chem., 1991, 12, 320.
60. P. G. Llabres O. Dideberg and L. Dupont, Acta Crystallogr., Sect. B, 1972, 28, 2438.
61. 6, δ(12) 471.5).
62. G. M. Sheldrick, Crystallographic Computing, vol. 3, Oxford University Press, Oxford, 1985, p. 175.
63. M. Watanabe, M. Date, M. Tsukazaki and S. Furukawa, Chem. Pharm. Bull., 1989, 37, 36.
64. W. Lohner and K. Praefcke, J. Organomet. Chem., 1981, 208, 39.
65. W. Lohner and K. Praefcke, J. Organomet. Chem., 1981, 205, 167.
66. B. R. Muth, Chem. Ber., 1960, 93, 283.