Conformational properties and chiroptical spectra of lactams and thiolactams with 2-azabicyclo[2.2.1]heptane, 2- and 3-azabicyclo[3.2.1]octane skeletons

Tetrahedron Asymmetry

Volumn 10, Issue 13, 1999, Pages 2591-2604

  Połoński, Tadeusz ^a   Milewska, Maria J ^a   Konitz, Antoni ^a,b   Gdaniec, Maria ^c  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF GDA SK   (Poland)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.1]OCTANE DERIVATIVE; LACTAM DERIVATIVE; NORBORNANE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHIRALITY; CHROMATOPHORE; CIRCULAR DICHROISM; CONCENTRATION (PARAMETERS); CONFORMATION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 0033516448     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00262-1     Document Type: Article

References (52)

1. 1. (a) Woody, R. W. In Circular Dichroism. Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R. W., Eds.; VCH: New York, 1994; Chapter 17.
2. (b) Rodger, A.; Norden, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, 1997; Chapter 2.
3. (c) Klyne, W.; Kirk, D. N.; Tilley, J.; Suginome, H. Tetrahedron 1980, 36, 543.
4. 2. Jackman, L. M.; Webb, R. L.; Yick, H. C. J Org. Chem. 1982, 47, 1824 and references cited therein.
5. 3. Richardson, F. S.; Strickland, R.; Shillady, D. D. J. Phys. Chem. 1973, 77, 248.
6. 4. (a) Bash, H.; Robin, M. B.; Kuebler, N. A. J. Chem. Phys. 1967, 47, 1824.
7. (b) Barnes, D. G.; Rhodes, W. J. Chem. Phys. 1968, 48, 817.
8. 5. Clark, L. B. J. Am. Chem. Soc. 1995, 117, 7974.
9. 6. Urry, D. W. J. Phys. Chem. 1968, 72, 3035.
10. 7. Goodman, M.; Toniolo, C.; Falcetta, J. J. Am. Chem. Soc. 1969, 91, 1816.
11. 8. Kajtar, M.; Kajtar, J.; Maier, Zs.; Zewdu, M.; Hóllosi, M. Spectrochim. Acta 1992, 48A, 87.
12. 9. Milewska, M. J.; Gdaniec, M.; Połoński, T. Tetrahedron: Asymmetry 1997, 8, 1267.
13. 10. Maciejewski, A.; Steer, R. P. Chem, Rev. 1993, 93, 67.
14. 11. (a) Hosoya, H.; Tanaka, J.; Nagakura, S. Bull. Chem. Soc. Jpn. 1976, 63, 80.
15. (b) Sandström, J. Acta Chem. Scand. 1962, 16, 1616.
16. (c) Tsuboi, M.; Hirakawa, A. Y.; Hoshino, T.; Ishiguro, T. J. Mol. Spectrosc. 1976, 63, 80.
17. (d) Judge, R. H.; Moule, D. C. Can. J. Chem. 1987, 65, 2100.
18. 12. Noyes, W. A.; Potter, R. J. J. Am. Chem. Soc. 1915, 37, 189.
19. 13. Krow, G. R.; Szczepanski, S. Tetrahedron Lett. 1980, 21, 4593.
20. 14. Cottingham, R. W. J. Org. Chem. 1960, 25, 1473.
21. 15. (a) Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1978, 87, 223.
22. (b) For review see: Cava, M. P.; Levinson, M. J. Tetrahedron 1985, 41, 5061.
23. 16. Litman, B. J.; Schellman, J. A. J. Phys. Chem. 1965, 69, 978. (b) Schellman, J. A. Acc. Chem. Res. 1968, 1, 144.
24. 16. Litman, B. J.; Schellman, J. A. J. Phys. Chem. 1965, 69, 978. (b) Schellman, J. A. Acc. Chem. Res. 1968, 1, 144.
25. 17. Ong, E. C.; Cusachs, L. C.; Weigang, O. E. J. Chem. Phys. 1977, 67, 3289.
26. 18. Połoński, T. Tetrahedron 1983, 39, 3139; ibid 1985, 41, 611.
27. 18. Połoński, T. Tetrahedron 1983, 39, 3139; ibid 1985, 41, 611.
28. 19. (a) Wolf, H. Tetrahedron Lett. 1965, 1075 and 1966, 5151.
29. 19. (a) Wolf, H. Tetrahedron Lett. 1965, 1075 and 1966, 5151.
30. (b) Ogura, H.; Takayanagi, H.; Furuhata, K. Chem. Lett. 1973, 387.
31. (c) Ogura, H.; Takayanagi, H.; Kubo, K.; Furuhata, K. J. Am. Chem. Soc. 1973, 95, 8056.
32. 20. (a) Snatzke, G.; Snatzke, F. In Fundamental Aspects and Recent Developments in Optical Rotatory Dispersion and Circular Dichroism; Ciardelli, F.; Salvadori, P., Eds.; Heyden: London, 1973; Chapter 3.2.
33. (c) Snatzke, G. Angew. Chem., Int. Ed. Engl. 1979, 18, 363.
34. 21. (a) Snatzke, G.; Werner-Zamojska, F. Tetrahedron Lett. 1972, 4275.
35. (b) Kirk, D. N. J. Chem. Soc., Perkin Trans. 2 1977, 2122.
36. (c) Pulm, F.; Schramm, J.; Hormes, J.; Grimme, S.; Peyerimhoff, S. D. Chem. Phys. 1997, 224, 143.
37. 22. (a) Greenfield, N. J.; Fasman, G. D. J. Am. Chem. Soc. 1970, 92, 177.
38. (b) Geiger, R. E.; Wagniére, G. H. Helv. Chim. Acta 1975, 58, 738.
39. (c) Konno, T.; Meguro, H.; Tuzimura, K. Tetrahedron Lett. 1975, 1305.
40. (d) Meguro, H.; Konno, T.; Tuzimura, K. Tetrahedron Lett. 1975, 1309.
41. (e) Tichý, M.; Maloň, P.; Bláha, K. Coll. Czech. Chem. Commun. 1977, 42, 3591.
42. 23. Bláha, K.; Maloň, P.; Tichý, M.; Frič, I.; Usha, R.; Ramakumar, S.; Venkatesan, K. Coll. Czech. Chem. Commun. 1978, 43, 3241.
43. 24. Gdaniec, M. unpublished results.
44. 25. Shustov, G. V.; Kadorkina, G. K.; Varlamov, S. V.; Kachanov, A. V.; Kostyanovsky, R. G.; Rauk, A. J. Am. Chem. Soc. 1992, 114, 1616.
45. 26. (a) Harada, N.; Nakanishi, K. Acc. Chem. Res. 1972, 5, 257.
46. (b) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, 1983.
47. 27. Frič, I.; Maloň, P.; Tichý, M.; Bláha, K. Coll. Czech. Chem. Commun. 1977, 42, 678.
48. 28. Robin, M. B. Higher Excited States of Polyatomic Molecules; Academic Press: Orlando, 1975; Vol. 2.
49. 29. Caamano, O.; Fernández, F.; Gómez, G.; Nieto, I. Tetrahedron 1994, 50, 2175.
50. 30. Suginome, H.; Furukawa, K.; Orito, K. J. Chem. Soc. Perkin Trans. 1 1991, 917.
51. 31. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, 46, 467.
52. 32. Sheldrick, G. M. SHELXL-93, University of Göttingen, 1993.