Collect. Czech. Chem. Commun. 2006, 71, 1278-1302
https://doi.org/10.1135/cccc20061278

A New Bis-Tröger's Base: Synthesis, Spectroscopy, Crystal Structure and Isomerization

Martin Valíka, Pavel Matějkaa, Eberhardt Herdtweckb, Vladimír Krála and Bohumil Dolenskya,*

a Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b Department of Inorganic Chemistry, Technische Universität München, Lichtenbergstraße 4, D-85747 Garching, Germany

References

1. Tröger J.: J. Prakt. Chem. 1887, 36, 225. <https://doi.org/10.1002/prac.18870360123>
2. Spielman M. A.: J. Am. Chem. Soc. 1935, 57, 583. <https://doi.org/10.1021/ja01306a060>
3a. Bag B. G.: Curr. Sci. 1995, 68, 279.
3b. Demeunynck M., Tatibouet A. in: Progress in Heterocycles Chemistry (G. W. Gribble and T. L. Cilchrist, Eds), p. 1–20. Pergamon, Oxford 1999.
4a. Goswami S., Ghosh K., Dasgupta S.: J. Org. Chem. 2000, 65, 1907. <https://doi.org/10.1021/jo9909204>
4b. Hansson A. P., Norrby P.-O., Wärnmark K.: Tetrahedron Lett. 1998, 39, 4565. <https://doi.org/10.1016/S0040-4039(98)00807-7>
4c. Wilcox C. S., Greer L. M., Lynch V.: J. Am. Chem. Soc. 1987, 109, 1865. <https://doi.org/10.1021/ja00240a049>
5a. Allen P. R., Reek J. N. H., Try A. C., Crossley M. J.: Tetrahedron: Asymmetry 1997, 8, 1161. <https://doi.org/10.1016/S0957-4166(97)00116-X>
5b. Webb T. H., Suh H., Wilcox C. S.: J. Am. Chem. Soc. 1991, 113, 8554. <https://doi.org/10.1021/ja00022a070>
5c. Wilcox C. S., Adrian J. C., Webb T. H., Zawacki F. J.: J. Am. Chem. Soc. 1992, 114, 10189. <https://doi.org/10.1021/ja00052a016>
6a. Baldeyrou B., Tardy C., Bailly C., Colson P., Houssier C., Charmantray F., Demeunynck M.: Eur. J. Med. Chem. 2002, 37, 315. <https://doi.org/10.1016/S0223-5234(02)01356-9>
6b. Johnson R. A., Gorman R. R., Wnuk R. J., Crittenden N. J., Aiken J. W.: J. Med. Chem. 1993, 36, 3202. <https://doi.org/10.1021/jm00073a023>
6c. Bailly C., Laine W., Demeunynck M., Lhomme J.: Biochem. Biophys. Res. Commun. 2000, 273, 681. <https://doi.org/10.1006/bbrc.2000.2997>
7a. Pardo C., Sesmilo E., Gutierrez-Puebla E., Monge A., Elguero J., Fruchier A.: J. Org. Chem. 2001, 66, 1607. <https://doi.org/10.1021/jo0010882>
7b. Mas T., Pardo C., Salort F., Elguero J., Torres M. R.: Eur. J. Org. Chem. 2004, 1097. <https://doi.org/10.1002/ejoc.200300645>
8. Valík M., Dolenský B., Petříčková H., Král V.: Collect. Czech. Chem. Commun. 2002, 67, 609. <https://doi.org/10.1135/cccc20020609>
9. Dolenský B., Valík M., Sýkora D., Král V.: Org. Lett. 2005, 7, 67. <https://doi.org/10.1021/ol047902f>
10a. Hansson A., Wixe T., Bergquist K.-E., Wärnmark K.: Org. Lett. 2005, 7, 2019. <https://doi.org/10.1021/ol050513g>
10b. Artacho J., Nilsson P., Bergquist K.-E., Wendt O. F., Wärnmark K.: Chem. Eur. J. 2006, 12, 2692. <https://doi.org/10.1002/chem.200501174>
11. Wagner E. C.: J. Org. Chem. 1937, 2, 157. <https://doi.org/10.1021/jo01225a003>
12a. Cudero J., Jiménez P., Marcos C., Pardo C., Ramos M., Elguero J., Fruchier A.: Magn. Reson. Chem. 1996, 34, 318. <https://doi.org/10.1002/(SICI)1097-458X(199604)34:4<318::AID-OMR861>3.0.CO;2-9>
12b. Pardo C., Ramos M., Fruchier A., Elguero J.: Magn. Reson. Chem. 1996, 34, 708. <https://doi.org/10.1002/(SICI)1097-458X(199609)34:9<708::AID-OMR949>3.0.CO;2-R>
12c. Elguero J., Fruchier A., Mas T., Pardo C.: Magn. Reson. Chem. 2005, 43, 665. <https://doi.org/10.1002/mrc.1619>
13. SpecTool 2.1, A Hypermedia Book for Structure Elucidation of Organic Compounds with Spectroscopic Methods. Chemical Concepts GmbH, Weinheim 1994.
14a. Prelog V., Wieland P.: Helv. Chim. Acta 1944, 27, 1127. <https://doi.org/10.1002/hlca.194402701143>
14b. Greenberg A., Molinaro N., Lang M.: J. Org. Chem. 1984, 49, 1127. <https://doi.org/10.1021/jo00180a035>
14c. Trapp O., Schurig V.: J. Am. Chem. Soc. 2000, 122, 1424. <https://doi.org/10.1021/ja991184o>
14d. Trapp O., Trapp G., Kong J., Hahn U., Vögtle F., Schurig V.: Chem. Eur. J. 2002, 8, 3629. <https://doi.org/10.1002/1521-3765(20020816)8:16<3629::AID-CHEM3629>3.0.CO;2-8>
15. Valík M., Dolenský B., Herdtweck E., Král V.: Tetrahedron: Asymmetry 2005, 16, 1969. <https://doi.org/10.1016/j.tetasy.2005.04.016>
16a. Harmata M.: Acc. Chem. Res. 2004, 37, 862. <https://doi.org/10.1021/ar030164v>
16b. Klärner F.-G., Kahlert B.: Acc. Chem. Res. 2003, 36, 919. <https://doi.org/10.1021/ar0200448>
16c. Klärner F.-G., Burkert U., Kamieth M., Boese R.: J. Phys. Org. Chem. 2000, 13, 604. <https://doi.org/10.1002/1099-1395(200010)13:10<604::AID-POC271>3.0.CO;2-7>
17a. Data Collection Software for NONIUS κ-CCD Devices, Delft 1997.
17b. Otwinowski Z., Minor W.: Methods Enzymol. 1997, 276, 307. <https://doi.org/10.1016/S0076-6879(97)76066-X>
17c. Hahn Th., Wilson A. J. C. (Eds): International Tables for Crystallography. Kluwer Academic Publisher, Dordrecht, Boston, London 1992.
17d. Artus G., Scherer W., Priermeier T., Herdtweck E.: STRUX-V, A Program System to Handle X-Ray Data. TU München, Garching 1997.
17e. Spek A. L.: PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht 2001.
17f. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M. C., Polidori G., Camalli M.: SIR92; J. Appl. Crystallogr. 1994, 27, 435.
17g. Sheldrick G. M.: SHELXL97. University of Göttingen, Göttingen 1998.