A new rotane family: Synthesis, structure, conformation, and dynamics of [3.4]-, [4.4]-, [5.4]-, and [6.4]rotane

Journal of the American Chemical Society

Volumn 120, Issue 2, 1998, Pages 317-328

  Fitjer, Lutz ^a   Steeneck, Christoph ^a   Gaini Rahimi, Said ^a   Schröder, Ulrike ^a   Justus, Karl ^a   Puder, Peter ^a   Dittmer, Martin ^a   Hassler, Carla ^a   Weiser, Jürg ^a   Noltemeyer, Mathias ^a   Teichert, Markus ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE; ROTANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY;

EID: 17344365212     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973118x     Document Type: Article

References (53)

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3. Preliminary communications: (a) Fitjer, L.; Quabeck, U. Angew. Chem. 1987, 99, 1054-1056; Angew. Chem., Int. Ed. Engl. 1987, 26, 1023-1025. (b) Fitjer, L.; Justus, K.; Puder, P.; Dittmer, M.; Hassler, C.; Noltemeyer, M. Angew. Chem. 1991, 103, 431-433; Angew. Chem., Int. Ed. Engl. 1991, 30, 436-438.
4. Preliminary communications: (a) Fitjer, L.; Quabeck, U. Angew. Chem. 1987, 99, 1054-1056; Angew. Chem., Int. Ed. Engl. 1987, 26, 1023-1025. (b) Fitjer, L.; Justus, K.; Puder, P.; Dittmer, M.; Hassler, C.; Noltemeyer, M. Angew. Chem. 1991, 103, 431-433; Angew. Chem., Int. Ed. Engl. 1991, 30, 436-438.
5. Preliminary communications: (a) Fitjer, L.; Quabeck, U. Angew. Chem. 1987, 99, 1054-1056; Angew. Chem., Int. Ed. Engl. 1987, 26, 1023-1025. (b) Fitjer, L.; Justus, K.; Puder, P.; Dittmer, M.; Hassler, C.; Noltemeyer, M. Angew. Chem. 1991, 103, 431-433; Angew. Chem., Int. Ed. Engl. 1991, 30, 436-438.
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20. For other examples including cases of conformational isomerism see: (a) Fitjer, L.; Klages, U.; Kühn, W.; Stephenson, D. S.; Binsch, G.; Noltemeyer, M.; Egert, E.; Sheldrick, G. M. Tetrahedron 1984, 40, 4337-4349. (b) Wehle, D.; Fitjer, L. Tetrahedron Lett. 1986, 27, 5843-5846. (c) Fitjer, L.; Giersig, M.; Wehle, D.; Dittmer, M.; Koltermann, G.-W.; Schormann, N.; Egert, E. Tetrahedron 1988, 44, 393-404. (d) Fitjer, L.; Klages, U.; Wehle, D.; Giersig, M.; Schormann, N.; Clegg, W.; Stephenson, D. S.; Binsch, G. Tetrahedron 1988, 44, 405-416.
21. For other examples including cases of conformational isomerism see: (a) Fitjer, L.; Klages, U.; Kühn, W.; Stephenson, D. S.; Binsch, G.; Noltemeyer, M.; Egert, E.; Sheldrick, G. M. Tetrahedron 1984, 40, 4337-4349. (b) Wehle, D.; Fitjer, L. Tetrahedron Lett. 1986, 27, 5843-5846. (c) Fitjer, L.; Giersig, M.; Wehle, D.; Dittmer, M.; Koltermann, G.-W.; Schormann, N.; Egert, E. Tetrahedron 1988, 44, 393-404. (d) Fitjer, L.; Klages, U.; Wehle, D.; Giersig, M.; Schormann, N.; Clegg, W.; Stephenson, D. S.; Binsch, G. Tetrahedron 1988, 44, 405-416.
22. For other examples including cases of conformational isomerism see: (a) Fitjer, L.; Klages, U.; Kühn, W.; Stephenson, D. S.; Binsch, G.; Noltemeyer, M.; Egert, E.; Sheldrick, G. M. Tetrahedron 1984, 40, 4337-4349. (b) Wehle, D.; Fitjer, L. Tetrahedron Lett. 1986, 27, 5843-5846. (c) Fitjer, L.; Giersig, M.; Wehle, D.; Dittmer, M.; Koltermann, G.-W.; Schormann, N.; Egert, E. Tetrahedron 1988, 44, 393-404. (d) Fitjer, L.; Klages, U.; Wehle, D.; Giersig, M.; Schormann, N.; Clegg, W.; Stephenson, D. S.; Binsch, G. Tetrahedron 1988, 44, 405-416.
23. For other examples including cases of conformational isomerism see: (a) Fitjer, L.; Klages, U.; Kühn, W.; Stephenson, D. S.; Binsch, G.; Noltemeyer, M.; Egert, E.; Sheldrick, G. M. Tetrahedron 1984, 40, 4337-4349. (b) Wehle, D.; Fitjer, L. Tetrahedron Lett. 1986, 27, 5843-5846. (c) Fitjer, L.; Giersig, M.; Wehle, D.; Dittmer, M.; Koltermann, G.-W.; Schormann, N.; Egert, E. Tetrahedron 1988, 44, 393-404. (d) Fitjer, L.; Klages, U.; Wehle, D.; Giersig, M.; Schormann, N.; Clegg, W.; Stephenson, D. S.; Binsch, G. Tetrahedron 1988, 44, 405-416.
24. Gleiter, R.; Haider, R.; Conia, J. M.; Barnier, J. P.; de Meijere, A.; Weber, W. J. Chem. Soc., Chem. Commun. 1979, 130-132.
25. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
26. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
27. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
28. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
29. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
30. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
31. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
32. Crystal structures: (a) Pascard, C.; Prange, T.; de Meijere, A.; Weber, W.; Barnier, J. P.; Conia, J. M. J. Chem. Soc., Chem. Commun. 1979, 425- 426. (b) Prance, T.; Pascard, C.; de Meijere, A.; Behrens, U.; Barnier, J. P.; Conia, J. M. Nouv. J. Chim. 1980,4, 321-327. (c) Boese, R.; Miebach, T.; de Meijere, A. J. Am. Chem. Soc. 1991, 113, 1743-1748. Calculations: (d) Randic, M.; Jakab, L. Croat. Chem. Acta 1970, 42, 425-432. (e) Kovacevic, K.; Maksic, Z. B.; Mogus, A. Croat. Chem. Acta 1979, 52, 249-263. (f) Ioffe, A. I.; Svyatkin, V. A.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 801-807; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987, 727-733. (g) Aped, P.; Allinger, N. L. J. Am. Chem. Soc. 1992, 114, 1-16.
33. (a) Fitjer, L.; Wehle, D. Angew. Chem. 1979, 91, 927-928; Angew. Chem., Int. Ed. Engl. 1979, 18, 868-869.
34. (a) Fitjer, L.; Wehle, D. Angew. Chem. 1979, 91, 927-928; Angew. Chem., Int. Ed. Engl. 1979, 18, 868-869.
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36. Nomenclature: (a) Zefirov, N. S.; Kozhushkov, S. L; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Trach, S. S. J. Am. Chem. Soc. 1990, 112, 7702-7707. (b) Zefirov, N. S.; Kutznetsova, T. S.; Eremenko, O. V.; Kokoreva, O. V.; Zatonsky, G.; Ugrak, B. I. J. Org. Chem. 1994, 59, 4087-4089. Recent reviews: (c) Zefirov, N. S.; Kuznetsova, T. S.; Zefirov, A. N. Izv. Akad. Nauk, Ser. Khim. 1995, 44, 1613-1621; Russ. Chem. Bull. 1995, 44, 1543-1552. (d) de Meijere, A.; Kozhushkov, S. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: London 1995; Vol. 4, pp 225-282.
37. Nomenclature: (a) Zefirov, N. S.; Kozhushkov, S. L; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Trach, S. S. J. Am. Chem. Soc. 1990, 112, 7702-7707. (b) Zefirov, N. S.; Kutznetsova, T. S.; Eremenko, O. V.; Kokoreva, O. V.; Zatonsky, G.; Ugrak, B. I. J. Org. Chem. 1994, 59, 4087-4089. Recent reviews: (c) Zefirov, N. S.; Kuznetsova, T. S.; Zefirov, A. N. Izv. Akad. Nauk, Ser. Khim. 1995, 44, 1613-1621; Russ. Chem. Bull. 1995, 44, 1543-1552. (d) de Meijere, A.; Kozhushkov, S. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: London 1995; Vol. 4, pp 225-282.
38. Nomenclature: (a) Zefirov, N. S.; Kozhushkov, S. L; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Trach, S. S. J. Am. Chem. Soc. 1990, 112, 7702-7707. (b) Zefirov, N. S.; Kutznetsova, T. S.; Eremenko, O. V.; Kokoreva, O. V.; Zatonsky, G.; Ugrak, B. I. J. Org. Chem. 1994, 59, 4087-4089. Recent reviews: (c) Zefirov, N. S.; Kuznetsova, T. S.; Zefirov, A. N. Izv. Akad. Nauk, Ser. Khim. 1995, 44, 1613-1621; Russ. Chem. Bull. 1995, 44, 1543-1552. (d) de Meijere, A.; Kozhushkov, S. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: London 1995; Vol. 4, pp 225-282.
39. Nomenclature: (a) Zefirov, N. S.; Kozhushkov, S. L; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Trach, S. S. J. Am. Chem. Soc. 1990, 112, 7702-7707. (b) Zefirov, N. S.; Kutznetsova, T. S.; Eremenko, O. V.; Kokoreva, O. V.; Zatonsky, G.; Ugrak, B. I. J. Org. Chem. 1994, 59, 4087-4089. Recent reviews: (c) Zefirov, N. S.; Kuznetsova, T. S.; Zefirov, A. N. Izv. Akad. Nauk, Ser. Khim. 1995, 44, 1613-1621; Russ. Chem. Bull. 1995, 44, 1543-1552. (d) de Meijere, A.; Kozhushkov, S. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: London 1995; Vol. 4, pp 225-282.
40. Nomenclature: (a) Zefirov, N. S.; Kozhushkov, S. L; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Trach, S. S. J. Am. Chem. Soc. 1990, 112, 7702-7707. (b) Zefirov, N. S.; Kutznetsova, T. S.; Eremenko, O. V.; Kokoreva, O. V.; Zatonsky, G.; Ugrak, B. I. J. Org. Chem. 1994, 59, 4087-4089. Recent reviews: (c) Zefirov, N. S.; Kuznetsova, T. S.; Zefirov, A. N. Izv. Akad. Nauk, Ser. Khim. 1995, 44, 1613-1621; Russ. Chem. Bull. 1995, 44, 1543-1552. (d) de Meijere, A.; Kozhushkov, S. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd.: London 1995; Vol. 4, pp 225-282.
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42. (a) de Meijere, A.; Kozhushkov, S.; Puls, C.; Haumann, T.; Boese, R.; Cooney, M. J.; Scott, L. T. Angew: Chem. 1994, 106, 934-936; Angew. Chem., Int. Ed. Engl. 1994, 33, 869-871.
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45. We use the term "conformational isomerism" in the sense defined by Dale (Dale, J. Stereochemie und Konformationsanalyse; Verlag Chemie: Weinheim, 1978). For this and other definitions, see also: Ernst, L. Chem. Unserer Zeit 1983, 17, 21.
46. We use the term "conformational isomerism" in the sense defined by Dale (Dale, J. Stereochemie und Konformationsanalyse; Verlag Chemie: Weinheim, 1978). For this and other definitions, see also: Ernst, L. Chem. Unserer Zeit 1983, 17, 21.
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52. (a) Trost, B. M.; Keeley, D. E.; Arndt, H. C.; Rigby, J. H.; Bagdanowicz, M. J. J. Am. Chem. Soc. 1977, 99, 3080-3087.
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