Novel Liquid Crystalline Compounds Containing Bicyclo[3.1.0]hexane Core Units

European Journal of Organic Chemistry

Volumn , Issue 2, 2004, Pages 289-303

  Kozhushkov, Sergei I ^a   Langer, Rainer ^a   Yufit, Dmitrii S ^b   Howard, Judith A K ^b   Schill, Heiko ^a   Demus, Dietrich ^c   Miyazawa, Kazutoshi ^d   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b DURHAM UNIVERSITY   (United Kingdom)

^c ISCO   (Germany)

^d CHISSO CORPORATION   (Japan)

Author keywords

Cross coupling; Cycloadditions; Liquid crystals; Small ring systems; Structure elucidation

Indexed keywords

3 (2 ETHYL) 6 PENTYLBICYCLO[3.1.0]HEXYL DERIVATIVE; 4 ETHOXY 2,3 DIFLUOROBENZALDEHYDE; 6 (4 CYANOPHENYL) 3 PENTYLBICYCLO[3.1.0]HEXANE; ACETIC ACID; BICYCLO COMPOUND; BICYCLO[3.1.0]HEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; HEXANE; LEAD; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CRYSTALLIZATION; CYCLOPROPANATION; DIASTEREOISOMER; FLUORINATION; LIQUID CRYSTAL; MELTING POINT; PHASE TRANSITION;

EID: 0842327451     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300448     Document Type: Article

References (75)

1. [1a] F. Reinitzer, Monatsh. Chem. 1888, 9, 421-441.
2. [1b] O. Lehmann, Z. Physik. Chem. 1889, 4, 462.
3. J. W. Goodby, G. W. Gray, Physical Properties of Liquid Crystals (Eds.: D. Demus, J. W. Goodby, G. W. Gray, H.-W. Spiess, V. Vill), Wiley-VCH, Weinheim, 1999, p. 17 ff.
4. O. Cervinka, O. Kirz, Z. Chem. 1971, 11, 63.
5. LiqCryst 4.4, Database of Liquid Crystalline Compounds, Copyright Volker Vill and LCI Publisher, Hamburg 1995-2003, http://www.lci-publisher.com.
6. D. Demus, A. Hauser, in Selected Topics in Liquid Crystal Research (Ed.: H.-D. Koswig), Akademie-Verlag, Berlin, 1990, p. 19.
7. [6a] H. Abe, T. Tsujino, K. Araki, Y. Takeuchi, T. Haayama, Tetrahedron: Asymmetry 2002, 13, 1519-1528.
8. [6b] C. (Carfagna, L. Mariani, A. Musco, G. Sallese, R. Santi, J. Org. Chem. 1991, 56, 3924-3927.
9. [6c] G. A. Russell, J. J. McDonnel, P. R. Whittle, R. S. Givens, R. G. Keske, J. Am. Chem. Soc. 1971, 93, 1452-1466.
10. R. Langer, Diplomarbeit, University of Göttingen, 2000.
11. Reviews: [8a] O. G. Kulinkovich, A. de Meijere, Chem. Rev. 2000, 100, 2789-2834.
12. [8b] A. de Meijere, S. I. Kozhuskov, A. I. Savchenko, in Titanium and Zirconium in Organic Synthesis (Ed.: I. Marek), Wiley-VCH, Weinheim, 2002, pp. 390-434.
13. For the general method of preparation of such amines see also: A. de Meljere, C. M. Williams, A. Kourdioukov, S. V. Sviridov, V. Chaplinski, M. Kordes, A. I. Savchenko, C. Stratmann, M. Noltemeyer, Chem. Eur. J. 2002, 8, 3789-3801, and references cited therein.
14. [10a] R. F. Hudson, R. J. Withey, J. Chem. Soc., B 1966, 237-240.
15. [10b] Z. Ding, J. J. Tufariello, Synth. Commun 1990, 20, 227-230.
16. [11a] A. J. Hubert, A. F. Noels, A. J. Anciaux, P. Teyssie, Synthesis 1976, 600-602.
17. Reviews: [11b] M. P. Doyle, Chem. Rev. 1986, 86, 919-939.
18. [11c] M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalysts for Organic Synthesis with Diazo Compounds, Wiley, New York, 1997.
19. A. E. Greene, M.-J. Luche, J.-P. Depres, J. Am. Chem. Soc. 1983, 105, 2435-2439.
20. CCDC-214462 (exo,exo-9a), -214459 (endo,exo-18a), -214460 (exo,exo-18b), -214458 (exo,exo-38b), -214461 (exo,endo-38b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
21. The appropriately substituted aryl halides, phenols and oligofluorinated compounds were kindly supplied by the Chisso Petrochemical Corporation. We are indebted to Dr. R. Tarao for his support.
22. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158-163.
23. The application of this coupling to substituted cyclohexylmagnesium bromides has been reported: [16a] N. A. Bumagin, E. V. Luzikova, J. Organomet. Chem. 1997, 532, 271-274.
24. [16b] N. A. Bumagin, E. V. Luzikova, I. P. Beletskaya, Russ. J. Org. Chem. (Engl. Transl.) 1995, 31, 1487-1491; Zh. Org. Khim. 1995, 31, 1657-1662.
25. [16b] N. A. Bumagin, E. V. Luzikova, I. P. Beletskaya, Russ. J. Org. Chem. (Engl. Transl.) 1995, 31, 1487-1491; Zh. Org. Khim. 1995, 31, 1657-1662.
26. A. Maercker, R. Geuß, Chem. Ber. 1973, 106, 773-797.
27. S. Winstein, E. C. Friedric, R. Baker, Y. Lin, Tetrahedron Suppl. 1966, 8, 621-645.
28. P. E. O'Bannon, W. P. Dailey, Tetrahedron 1990, 46, 7341-7358.
29. [20a] R. L. Cook, T. B. Malloy, Jr., J. Am. Chem. Soc. 1974, 96, 1703-1707.
30. [20b] V. S. Mastryukov, E. L. Osina, L. V. Vilkov, R. L. Hilderbrandt, J. Am. Chem. Soc. 1977, 99, 6855-6861.
31. [20c] Q. Shen, V. S. Mastryukov, J. E. Boggs, J. Mol. Struct. 1995, 352/353, 181-191.
32. [21a] P. Kang, J. Choo, M. Jeong, Y. Kwon, J. Mol. Struct. 2000, 519, 75-84.
33. [21b] R. Okazaki, J. Niwa, S. Kato, Bull. Chem. Soc. Jpn. 1988, 61, 1619-1624.
34. [21c] K. Siam, J. D. Ewbank, L. Schafer, C. Van Alsenoy, Theochem 1987, 35, 121-128.
35. [21d] p. N. Skancke, Theochem 1982, 3, 255-265.
36. [21e] P. J. Mjoberg, J. Almlof, Chem. Phys. 1978, 29, 201-208.
37. [22a] M. Tamura, J. Kochi, Synthesis 1971, 303-305.
38. [22b] K. C. Nicolaou, J. Li, G. Zenke, Helv. Chim. Acta 2000, 83, 1977-2006.
39. [23a] R. Paulissen, A. J. Hubert, P. Teyssie, Tetrahedron Lett. 1972, 1465-1466.
40. [23b] J. Kottwitz, H. Vorbrüggen, Synthesis 1975, 636-637.
41. For a review see also: [23c] Yu. V. Tomilov, V. A. Dokichev, U. M. Dzhemilev, O. M. Nefedov, Usp. Khim. 1993, 62, 847-886; Russ. Chem. Rev. 1993, 62, 799-838.
42. For a review see also: [23c] Yu. V. Tomilov, V. A. Dokichev, U. M. Dzhemilev, O. M. Nefedov, Usp. Khim. 1993, 62, 847-886; Russ. Chem. Rev. 1993, 62, 799-838.
43. [24a] G. L. Closs, R. A. Moss, J. Am. Chem. Soc. 1964, 86, 4042-4053.
44. G. L. Closs, S. H. Goh, J. Chem. Soc., Perkin Trans. 1 1972, 2103-2108.
45. [24c] R. J. Mohrbacher, N. H. Cromwell, J. Am. Chem. Soc. 1957, 79, 401-408.
46. [24d] T. Migita, K. Kurino, W. Ando, J. Chem. Soc., Perkin Trans. 2 1977, 1094-1097.
47. [24e] W. Ando, H. Higuchi, T. Migita, J. Org. Chem. 1977, 42, 3365-3372.
48. [24f] A. Oku, T-A. Yokoyama, T. Harada, J Org. Chem. 1983, 48, 5333-5337.
49. [24g] T. Gulbrandsen, P. Kolsaker, Acta Chem. Scand., Ser. B 1983, 37, 196-202.
50. [24h] G. Wu, M. Jones, R. Walton, P. M. Lahti, J. Org. Chem. 1998, 63, 5368-5371.
51. [25a] R. G. Salomon, M. F. Salomon, J. L. C. Kachinski, J. Am. Chem. Soc. 1977, 99, 1043-1054.
52. [25b] S. H. Goh, L. E. Closs, G. L. Closs, J. Org. Chem. 1969, 34, 25-31.
53. [25c] E. N. Marvell, C. Lin, J. Am. Chem. Soc. 1978, 100, 877-883.
54. M. F. Dull, P. G. Abend, J. Am. Chem. Soc. 1959, 81, 2588-2591.
55. V. K. Aggarwal, H. W. Smith, G. Hynd, R. V. H. Jones, R. Fieldhouse, S. E. Spey, J. Chem. Soc., Perkin Trans. 1 2000, 3267-3276.
56. X. Creary, J. Am. Chem. Soc. 1980, 45, 1611-1618.
57. Cambridge Crystallographic Database CSD Version 5.24 (Feb. 2003).
58. E. Vilsmaier, G. Milch, W. Roth, W. Frank, G. I. Reiss, J. Pract. Chem. Chem. Zeitung 1998, 340, 356-360.
59. Q. Shen, C. Wells, M. Traetteberg, R. K. Bohn, A. Willis, J. Knee, J. Org. Chem. 2001, 66, 5840-5845.
60. 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, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA, 1998.
61. [33a] W. D. Cornell, M. P. Ha, Y. Sun, P. A. Kollman, J. Comput. Chem. 1996, 17, 1541-1548.
62. [33b] L. A. Carreira, G. J. Liang, W. B. Peterson, J. N. Willis, J. Chem. Phys. 1972, 56, 1440-1443.
63. [34a] R. J. Abraham, R. Koniotou, F. Sancassan, J. Chem. Soc., Perkin Trans. 2 2002, 2025-2930, and references 2-9 cited therein.
64. [34b] B. Fuchs, Top. Stereochem. 1978, 10, 1-96, and references cited therein.
65. cf. F. H. Allen, J. P. M. Lommerse, V. J. Hoy, J. A. K. Howard, G. R. Desraju, Acta Crystallogr., Sect. B 1996, 52, 734-745.
66. Compound 39 was prepared in the Chisso Speciality Chemicals Research Center according to a published procedure: M. E. Neubert, Mol. Cryst. Liq. Cryst. 1982, 89, 93-117.
67. R. Eidenschink, D. Erdmann, J. Krause, L. Pohl, Angew. Chem. 1977, 89, 103-105; Angew. Chem. Int. Ed. Engl. 1977, 16, 100-103.
68. R. Eidenschink, D. Erdmann, J. Krause, L. Pohl, Angew. Chem. 1977, 89, 103-105; Angew. Chem. Int. Ed. Engl. 1977, 16, 100-103.
69. W. Maier, G. Meier, Z. Naturforsch., Teil A 1961, 16, 262-267.
70. M. Banwell, A. Edwards, J. Harvey, D. Hockless, A. Willis, J. Chem. Soc., Perkin Trans. 1 2000, 2175-2178.
71. A. G. Davies, D. Griller, K. U. Ingold, J. C. Walton, D. A. Lindsay, J. Chem. Soc., Perkin Trans. 2 1981, 633-641.
72. S. E. Cremer, C. Blankenship, J. Org. Chem. 1982, 47, 1626-1632.
73. G. A. Olah, G. K. S. Prakash, M. Arvanaghi, F. A. L. Anet, J. Am. Chem. Soc. 1982, 104, 7105-7108.
74. W. Lang, G. Alder, Ger. Patent 1097439, 1959; Chem. Abstr. 1962, 56, 354.
75. P.-L. Wu, S.-Y. Peng, J. Magrath, Synthesis 1996, 249-252.