Collect. Czech. Chem. Commun. 2000, 65, 1911-1938
https://doi.org/10.1135/cccc20001911

Dichotomy in the Ring Opening Reaction of 5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione with Cyclic Secondary Amines

Peter Šafářa,*, František Považaneca, Naďa Prónayováb, Peter Baranc, Guido Kickelbickd, Jozef Kožíšeke and Martin Brezaf

a Department of Organic Chemistry, Slovak Technical University, SK-812 37 Bratislava, Slovak Republic
b Central Laboratory, Slovak Technical University, SK-812 37 Bratislava, Slovak Republic
c Department of Chemistry, University of Cyril and Methodius, nám. J. Herdu 2, SK-917 01 Trnava, Slovak Republic
d Institut für Anorganische Chemie, Technische Universität Wien, Getreidemarkt 9/153, A-1060 Wien, Austria
e Department of Inorganic Chemistry, Slovak Technical University, SK-812 37 Bratislava, Slovak Republic
f Department of Physical Chemistry, Slovak Technical University, SK-812 37 Bratislava, Slovak Republic

References

1. Corey E. J., Cheng Hue Miu: The Logic of Chemical Synthesis. Wiley, New York 1989.
2. Mase T., Sodeoka M., Shibasaki M.: Tetrahedron Lett. 1984, 25, 5087. <https://doi.org/10.1016/S0040-4039(01)91126-8>
3. Piancatelli G., D’Auria M., D’Onofrio F.: Synthesis 1994, 9, 867. <https://doi.org/10.1055/s-1994-25591>
4. Bosshard P., Eugster C. H.: Adv. Heterocycl. Chem. 1966, 7, 378.
5a. Lewis K. G., Mulquiney C. E.: Aust. J. Chem. 1970, 23, 2315. <https://doi.org/10.1071/CH9702315>
5b. Lewis K. G., Mulquiney C. E.: Aust. J. Chem. 1979, 32, 1079. <https://doi.org/10.1071/CH9791079>
5c. D’Arcy B. R. D., Lewis K. G., Mulquiney C. E.: Aust. J. Chem. 1985, 38, 953. <https://doi.org/10.1071/CH9850953>
5d. D’Acy B. R. D., Lewis K. G., Mulquiney C. E.: Aust. J. Chem. 1987, 40, 509.
5e. Lewis K. G., Mulquiney C. E.: Aust. J. Chem. 1990, 43, 655. <https://doi.org/10.1071/CH9900655>
5f. Lewis K. G., Mulquiney C. E.: Tetrahedron 1977, 33, 463. <https://doi.org/10.1016/S0040-4020(77)80002-1>
6a. Šafář P., Považanec F., Zalibera Ľ., Berkeš D.: Collect. Czech. Chem. Commun. 1993, 58, 555. <https://doi.org/10.1135/cccc19930555>
6b. Šafář P., Čepec P., Považanec F., Koreňová A., Prónayová N.: Collect. Czech. Chem. Commun. 1994, 59, 2481. <https://doi.org/10.1135/cccc19942481>
7. Leditschke H.: Chem. Ber. 1952, 85, 483. <https://doi.org/10.1002/cber.19520850527>
8. Yasuda H., Hayashi T., Midorikawa H.: J. Org. Chem. 1970, 35, 1234. <https://doi.org/10.1021/jo00829a102>
9a. Wedner J., Vilsmaier E., Henn C.: Monatsh. Chem. 1987, 118, 1147. <https://doi.org/10.1007/BF00811288>
9b. Vilsmaier E., Joerg K., Nauert R.: Chem. Ber. 1984, 117, 2928. <https://doi.org/10.1002/cber.19841170913>
10. Lewis K. G.: J. Chem. Soc. 1959, 531.
11. Dillon A. P., Lewis K. G.: Tetrahedron 1969, 25, 2035. <https://doi.org/10.1016/S0040-4020(01)82824-6>
12. Krapivin G. D., Kulnevich V. G. I., Valter N. I.: Khim. Geterotsikl. Soedin. 1986, 10, 1325.
13. Nudelman N. S., Lewkowicz E., Furlong J. J. P.: J. Org. Chem. 1993, 58, 1847. <https://doi.org/10.1021/jo00059a042>
14. Kutney J. P., Hanssen H. W., Vijayakumaran Nair G.: Tetrahedron 1971, 27, 3323. <https://doi.org/10.1016/S0040-4020(01)97744-0>
15. Krapivin G. D., Valter N. I., Kaklugina T. Ya., Kulnevich V. G. I.: Khim. Geterotsikl. Soedin. 1994, 3, 327.
16. Sheldrick G. M.: Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1990, 46, 467. <https://doi.org/10.1107/S0108767390000277>
17. Sheldrick G. M.: SHELXL93. Program for Refinement of Crystal Structure. University of Göttingen, Göttingen 1993.
18. Nardelli M.: Comput. Chem. 1983, 7, 95. <https://doi.org/10.1016/0097-8485(83)85001-3>
19. Johnson C. K.: ORTEPII. Report ORNL-3794, revised. Oak Ridge National Laboratory, Oak Ridge (TN) 1971.
20. Dewar M. J. S., Thiel W.: Quantum Chem. Progr. Exchange 1986, 506.
21. Dewar M. J. S., Zoebish E. G., Healy E. F., Stewart J. J. P.: J. Am. Chem. Soc. 1985, 107, 3902. <https://doi.org/10.1021/ja00299a024>
22. Pople J. A., Beveridge D. L.: Approximate Molecular Orbital Theory. McGraw–Hill, New York 1970.