Abstract
The orthoamide derivative of phenylpropiolic acid reacts with tertiary CH-acidic compounds as alkylmalonic acid dialkylesters under formation of 1,1-diamino-allenes wich rearrange to give 2-alkoxycarbonyl-1,1-diamino-1,3-butadienes by migration of an alkoxycarbonyl group. Perchloric acid transforms these butadienes to amidinium perchlorates. The crystal structure of an amidinium perchlorate derived from cinnamic acid has been determined.
Funding source: MWK Baden-Württemberg
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: MWK Baden-Württemberg
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
Literatur
1. Kantlehner, W., Heckel, B., Mezger, J. Z. Naturforsch. 2020, 75b, 865–880. https://doi.org/10.1515/znb-2020-0072.Search in Google Scholar
2. Weingarten, H. Tetrahedron 1968, 24, 2767–2771; https://doi.org/10.1016/s0040-4020(01)82548-5.Search in Google Scholar
3. Kantlehner, W., Kreß, R., Mezger, J., Ladendorf, S. Z. Naturforsch. 2005, 60b, 227–230; https://doi.org/10.1515/znb-2005-0217.Search in Google Scholar
4. Kantlehner, W., Speh, P., Lehmann, H., Bräuner, H.-J., Haug, E., Mergen, W. W. Chem. Ztg. 1990, 114, 176–178.Search in Google Scholar
5. Kantlehner, W., Hauber, M., Vettel, M. J. Prakt. Chem. Chem. Ztg. 1996, 338, 403–413; https://doi.org/10.1002/prac.19963380180.Search in Google Scholar
6. Kantlehner, W., Vettel, M., Lehmann, H., Stieglitz, R., Ivanov, I. C. J. Prakt. Chem. 1998, 340, 408–423; https://doi.org/10.1002/prac.19983400503.Search in Google Scholar
7. Kantlehner, W., Stieglitz, R., Hauber, M., Haug, E., Regele, C. J. Prakt. Chem. 2000, 342, 256–268; https://doi.org/10.1002/(sici)1521-3897(200003)342:3<256::aid-prac256>3.0.co;2-g.10.1002/(SICI)1521-3897(200003)342:3<256::AID-PRAC256>3.0.CO;2-GSearch in Google Scholar
8. Kantlehner, W., Haug, E., Stieglitz, R., Frey, W., Kreß, R., Mezger, J. Z. Naturforsch. 2002, 57b, 399–419; https://doi.org/10.1515/znb-2002-0406.Search in Google Scholar
9. Kantlehner, W., Mezger, J., Kreß, R., Frey, W. Z. Naturforsch. 2018, 73b, 437–455; https://doi.org/10.1515/znb-2018-0011.Search in Google Scholar
10. Weingärtner, W., Kantlehner, W., Maas, G. Synthesis 2011, 43, 265–272 https://doi.org/10.1055/s-0030-1258353.Search in Google Scholar
11. Brown, M. H. US Patent 3214428, 1965. Chem. Abstr. 1966, 64, P3501h.Search in Google Scholar
12. Bredereck, H., Simchen, G., Horn, P. Chem. Ber. 1970, 103, 210–221; https://doi.org/10.1002/cber.19701030129.Search in Google Scholar
13. Eilingsfeld, H., Seefelder, M., Weidinger, H. Angew. Chem. 1960, 72, 836–845; https://doi.org/10.1002/ange.19600722208.Search in Google Scholar
14. Kiesel, M., Haug, E., Kantlehner, W. J. Prakt. Chem. 1997, 339, 159–170; https://doi.org/10.1002/prac.19973390130.Search in Google Scholar
15. Kantlehner, W., Haug, E., Mergen, W. W., Speh, P., Maier, T., Kapassakalidis, J. J., Bräuner, H.-J., Hagen, H. Liebigs Ann. Chem. 1984, 108–126, https://doi.org/10.1002/jlac.198419840112.Search in Google Scholar
16. Vettel, M., Bräuner, H.-J., Kantlehner, W. Z. Naturforsch. 2018, 73b, 457–466; https://doi.org/10.1515/znb-2018-0022.Search in Google Scholar
17. Kantlehner, W., Edelmann, K., Frey, W. Z. Naturforsch. 2018, 73b, 623–634; https://doi.org/10.1515/znb-2018-0064.Search in Google Scholar
18. Kantlehner, W., Mezger, J., Lehmann, H., Edelmann, K., Frey, W. Z. Naturforsch. 2018, 73b, 689–702; https://doi.org/10.1515/znb-2018-0065.Search in Google Scholar
19. Kantlehner, W., Lehmann, H., Stieglitz, R., Frey, W. Z. Naturforsch. 2019, 74b, 925–938; https://doi.org/10.1515/znb-2019-0078.Search in Google Scholar
20. Kantlehner, W., Stieglitz, R., Lehmann, H., Vettel, M. Z. Naturforsch. 2019, 74b, 913–924; https://doi.org/10.1515/znb-2019-0077.Search in Google Scholar
21. Kantlehner, W., Lehmann, H., Stieglitz, R. ARKIVOC 2012, 442–456. https://doi.org/10.3998/ark.5550190.0013.330.Search in Google Scholar
22. Viehe, H. G., Janousek, Z., Gompper, R., Lach, D. Angew Chem. Int. Ed. Engl. 1973, 12, 566–567; https://doi.org/10.1002/anie.197305661.Search in Google Scholar
23. Maas, G., Würthner, E., Singer, B., Mayer, T., Krauss, D. Chem. Ber. 1989, 122, 2311–2317; https://doi.org/10.1002/cber.19891221218.Search in Google Scholar
24. Saalfrank, R. W., Rost, W. Angew Chem. Int. Ed. Engl. 1983, 22, 321; https://doi.org/10.1002/anie.198303211.Search in Google Scholar
25. Saalfrank, R. W., Hilbig, K., Schütz, F., Peters, K., von Schnering, H. G. Chem. Ber. 1988, 121, 1291–1297; https://doi.org/10.1002/cber.19881210713.Search in Google Scholar
26. Saalfrank, R. W., Schütz, F., Moenius, U. Synthesis 1985, 17, 1062–1067; https://doi.org/10.1055/s-1985-31430.Search in Google Scholar
27. Silverstein, R. M., Bassler, G. C., Morill, T. C. Spectrametric Identification of Organic Compounds; Wiley: New York, Chichester, Brisbane, Toronto, Singapore, 1981; pp. S. 318.Search in Google Scholar
28. Tinant, B., Declerq, J.-P., Bouvy, D., Janousek, Z., Viehe, H. G. J. Chem. Soc. Perkin Trans 2. 1993, 2, 911–915; https://doi.org/10.1039/p29930000911.Search in Google Scholar
29. Lehmann, H. Beiträge zur Chemie von Orthoamiden von Alkincarbonsäuren. Dissertation, Universität Stuttgart: Stuttgart, 1991.Search in Google Scholar
© 2020 Walter de Gruyter GmbH, Berlin/Boston