Solvent effects on the kinetics and diastereoselectivity of the intermolecular hetero Diels-Alder reaction of an enamino ketone with isopropenyl methyl ether under high pressure

Polish Journal of Chemistry

Volumn 71, Issue 12, 1997, Pages 1749-1762

  Tietze, L F ^a   Henrich, M ^a   Rothert, I ^a   Kuchta, G ^a   Buback, M ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Activation parameters; Enamino ketones; Hetero Diels Alder reactions; High pressure; Intermolecular; Solvent effects; Volume profiles

Indexed keywords

EID: 0031328589     PISSN: 01375083     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
2. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
3. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
4. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
5. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
6. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
7. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
8. Winter R. and Jonas J., High Pressure Chemistry, Biochemistry and Materials Science, Kluwer Academic Publishers, Dordrecht 1993; Isaacs N.S., Tetrahedron, 47, 8463 (1991); Matsumoto K. and Acheson R.M., Organic Synthesis at High Pressures, Wiley-Interscience, New York 1991; Klärner F.-G., Chem. Unserer Zeit, 23, 53 (1989); van Eldik R., Asano T. and le Noble W.J., Chem. Rev., 89, 549 (1989); Jurczak J. and Baranowski B., High Pressure Chemical Synthesis, Elsevier, Amsterdam 1988; Matsumoto K., Sera A. and Uchida T., Synthesis, 1 (1985); Matsumoto K. and Sera A., Synthesis, 999 (1985).
9. Buback M., Tost W., Tietze L.F. and Voß E., Chem. Ber., 121, 781 (1988).
10. Buback M., Tost W., Hübsch T., Voß E. and Tietze L.F., Chem. Ber., 122, 1179 (1988).
11. Tietze L.F., Hübsch T., Oelze J., Ott C., Tost W., Wörner G. and Buback M., Chem. Ber., 125, 2249 (1992).
12. Tietze L.F., Hübsch T., Ott C., Kuchta G. and Buback M., Liebigs Ann., 1 (1995).
13. Buback M., Kuchta G., Niklaus A., Henrich M., Rothert I. and Tietze L.F., Liebigs Ann., 1151 (1996).
14. Buback M., Gerke K., Ott C. and Tietze L.F., Chem. Ber., 127, 2241 (1994).
15. Buback M., Abeln J., Hübsch T, Ott C. and Tietze L.F., Liebigs Ann., 9 (1995).
16. Heiner T., Michalski S., Gerke K., Kuchta G., Buback M. and de Meijere A., Synlett., 4, 355 (1995).
17. Tost W., Doctoral Thesis, Universität Göttingen, Germany 1989.
18. El'yanov B.S. and Gonikberg E.M., J. Chem. Soc., Farad. Trans. 1, 75, 172 (1979).
19. El'yanov B.S., Gonikberg E.M. and Jenner G., J. Chem. Soc., Perkin Trans. 2, 137 (1992).
20. Kezdy F.J., Jaz J. and Bruylants A., Bull. Soc. Chim. Belg., 67, 687 (1958).
21. Swinbourne E.S., J. Chem. Soc., 2371 (1960).
22. Tietze L.F., Hübsch T., Buback M. and Tost W., High Press. Res., 5, 638 (1990).
23. Kuchta G., Doctoral Thesis, Universität Göttingen, Germany 1994.
24. Reichardt C., "Solvents and Solvent Effects in Organic Chemistry", VCH Verlagsgesellschaft, Weinheim, 1990.
25. Isaacs N.S., "Liquid Phase High Pressure Chemistry", J. Wiley & Sons, Chichester-New York-Brisbane-Toronto, 1981.
26. Jenner G., Ang. Chem., 87, 186 (1975); Sauer J. and Sustmann R., Angew. Chem., 92, 773 (1980).
27. Jenner G., Ang. Chem., 87, 186 (1975); Sauer J. and Sustmann R., Angew. Chem., 92, 773 (1980).
28. Asano A. and Okada T., J. Phys. Chem., 88, 238 (1984).
29. Tiltscher H. and Hofmann H., Chem. Eng. Sci., 42, 959 (1987).
30. Schornack L.G. and Eckert C.A., J. Phys. Chem., 74, 3014 (1970).
31. Francesconi A.Z., Franck E.U. and Lentz H., Ber. Bunsenges. Phys. Chem., 79, 897 (1975).
32. le Noble W.J. and Kelm H., Angew. Chem., 92, 887 (1980).
33. Klärner F.-G., Krawczyk B., Ruster V. and Deiters U.K., J. Am. Chem. Soc., 116, 7646 (1994).
34. Firestone R.A. and Smith G.M., Chem. Ber., 122, 1089 (1989).