Diels-Alder and ene reactions of the stannaethene Me2Sn=c(SiMe3)2: Dienophilic and enophilic behaviour of ethenes Me2E=C(SiMe3)2 (E=Si, Ge, Sn)

Chemistry - A European Journal

Volumn 4, Issue 12, 1998, Pages 2571-2579

  Wiberg, Nils ^a   Wagner, Susanne ^a   Vasisht, Sham Kumar ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Dienophilicity; Enophilicity; Germanium; Silicon; Tin

Indexed keywords

ETHYLENE DERIVATIVE; GERMANIUM; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0031742459     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981204)4:12<2571::AID-CHEM2571>3.0.CO;2-4     Document Type: Article

References (41)

1. N. Wiberg, G. Preiner, Angew. Chem. 1977, 89, 343; Angew. Chem. Int. Ed. Engl. 1977, 16, 328.
2. N. Wiberg, G. Preiner, Angew. Chem. 1977, 89, 343; Angew. Chem. Int. Ed. Engl. 1977, 16, 328.
3. N. Wiberg in Organosilicon Chemistry II (Eds.: N. Auner, J. Weis), VCH, Weinheim, 1995, p. 367.
4. N. Wiberg, G. Preiner, G. Wagner, H. Köpf, Z. Naturforsch. B 1987, 42, 1055, 1062.
5. N. Wiberg, K. Schurz, G. Fischer, Chem. Ber. 1986, 119, 3498.
6. N. Wiberg, G. Fischer, K. Schurz, Chem. Ber. 1987, 120, 1605.
7. N. Wiberg, G. Fischer, S. Wagner, Chem. Ber. 1991, 124, 769.
8. N. Wiberg, S. Wagner, G. Fischer, Chem. Ber. 1991, 124, 1981.
9. N. Wiberg, S. Wagner, Z. Naturforsch. B 1996, 51, 629.
10. N. Wiberg, S. Wagner, Z. Naturforsch. B 1996, 51, 838.
11. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773; Angew. Chem. Int. Ed. Engl. 1980, 79, 779.
12. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773; Angew. Chem. Int. Ed. Engl. 1980, 79, 779.
13. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597; Angew. Chem. Int. Ed. Engl. 1969, 8, 556; W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506; Angew. Chem. Int. Ed. Engl. 1978, 17, 476; G. V. Boyd in The Chemistry of Double Bonded Functional Groups (Ed.: S. Patai), Wiley, London, 1989, p. 477.
14. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597; Angew. Chem. Int. Ed. Engl. 1969, 8, 556; W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506; Angew. Chem. Int. Ed. Engl. 1978, 17, 476; G. V. Boyd in The Chemistry of Double Bonded Functional Groups (Ed.: S. Patai), Wiley, London, 1989, p. 477.
15. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597; Angew. Chem. Int. Ed. Engl. 1969, 8, 556; W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506; Angew. Chem. Int. Ed. Engl. 1978, 17, 476; G. V. Boyd in The Chemistry of Double Bonded Functional Groups (Ed.: S. Patai), Wiley, London, 1989, p. 477.
16. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597; Angew. Chem. Int. Ed. Engl. 1969, 8, 556; W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506; Angew. Chem. Int. Ed. Engl. 1978, 17, 476; G. V. Boyd in The Chemistry of Double Bonded Functional Groups (Ed.: S. Patai), Wiley, London, 1989, p. 477.
17. H. M. R. Hoffmann, Angew. Chem. 1969, 81, 597; Angew. Chem. Int. Ed. Engl. 1969, 8, 556; W. Oppolzer, V. Snieckus, Angew. Chem. 1978, 90, 506; Angew. Chem. Int. Ed. Engl. 1978, 17, 476; G. V. Boyd in The Chemistry of Double Bonded Functional Groups (Ed.: S. Patai), Wiley, London, 1989, p. 477.
18. K. N. Houk, Acc. Chem. Res. 1975, 8, 361, and references therein.
19. R. B. Woodward, R. Hoffmann. Angew. Chem. 1969, 81, 797; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
20. R. B. Woodward, R. Hoffmann. Angew. Chem. 1969, 81, 797; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
21. N. Wiberg, S.-K, Vasisht, Angew. Chem. 1991, 103, 105; Angew. Chem. Int. Ed. Engl. 1991, 30, 93, and references therein.
22. N. Wiberg, S.-K, Vasisht, Angew. Chem. 1991, 103, 105; Angew. Chem. Int. Ed. Engl. 1991, 30, 93, and references therein.
23. N. Wiberg, S. Wagner, S.-K. Vasisht, unpublished results.
24. The ratio Diels - Alder/ene reaction is temperature dependent. For example, in the reaction of 2 with 2,3-dimethylbutadiene (formation of 5 and 6). the ratio of [4 + 2] main product to ene minor product decreases from 11:1 at -40°C to 6:1 at 130°C.
25. K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711; Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
26. K. N. Houk, Y. Li, J. D. Evanseck, Angew. Chem. 1992, 104, 711; Angew. Chem. Int. Ed. Engl. 1992, 31, 682.
27. N. Wiberg, G. Preiner, O. Schieda, G. Fischer, Chem. Ber. 1981, 114, 3518.
28. G. Trinquier, J. C. Barthelat, J. Satgé, J. Am. Chem. Soc. 1982, 104, 5931.
29. -1: R. S. Grev, Adv. Organomet. Chem. 1991, 33, 125.
30. S. D. Kahn, C. F. Pau, L. E. Overman, W. J. Hehre, J. Am. Chem. Soc. 1986, 108, 7381; P. V. Alston, R. M. Ottenbrite, J. Org. Chem. 1975, 40, 1111; O. Eisenstein, J. M. Lefour, N. T. Ahn, Tetrahedron 1977, 33, 523; H. U. Wagner, Institut für Organische Chemie der Universität München, unpublished AM1 calculations: Interchem, P. Bladon, Quantum Chemistry Program Exchange No. 626, Version 1994.
31. S. D. Kahn, C. F. Pau, L. E. Overman, W. J. Hehre, J. Am. Chem. Soc. 1986, 108, 7381; P. V. Alston, R. M. Ottenbrite, J. Org. Chem. 1975, 40, 1111; O. Eisenstein, J. M. Lefour, N. T. Ahn, Tetrahedron 1977, 33, 523; H. U. Wagner, Institut für Organische Chemie der Universität München, unpublished AM1 calculations: Interchem, P. Bladon, Quantum Chemistry Program Exchange No. 626, Version 1994.
32. S. D. Kahn, C. F. Pau, L. E. Overman, W. J. Hehre, J. Am. Chem. Soc. 1986, 108, 7381; P. V. Alston, R. M. Ottenbrite, J. Org. Chem. 1975, 40, 1111; O. Eisenstein, J. M. Lefour, N. T. Ahn, Tetrahedron 1977, 33, 523; H. U. Wagner, Institut für Organische Chemie der Universität München, unpublished AM1 calculations: Interchem, P. Bladon, Quantum Chemistry Program Exchange No. 626, Version 1994.
33. S. D. Kahn, C. F. Pau, L. E. Overman, W. J. Hehre, J. Am. Chem. Soc. 1986, 108, 7381; P. V. Alston, R. M. Ottenbrite, J. Org. Chem. 1975, 40, 1111; O. Eisenstein, J. M. Lefour, N. T. Ahn, Tetrahedron 1977, 33, 523; H. U. Wagner, Institut für Organische Chemie der Universität München, unpublished AM1 calculations: Interchem, P. Bladon, Quantum Chemistry Program Exchange No. 626, Version 1994.
34. Wiberg, K. Schurz, J. Organomet. Chem. 1988, 341, 145.
35. Holleman-Wiberg, Lehrbuch der Anorganischen Chemie, 101st ed., DeGruyter, 1995.
36. The Chemistry of Organic Silicon Compounds (Ed.: S. Patai), Wiley, 1989; M. J. S. Dewar, G. L. Grady, E. F. Healy, Organometallics 1987, 6, 186; M. J. S. Dewar, G. L. Grady, J. P. Stewart, J. Am. Chem. Soc. 1984, 106, 6771.
37. The Chemistry of Organic Silicon Compounds (Ed.: S. Patai), Wiley, 1989; M. J. S. Dewar, G. L. Grady, E. F. Healy, Organometallics 1987, 6, 186; M. J. S. Dewar, G. L. Grady, J. P. Stewart, J. Am. Chem. Soc. 1984, 106, 6771.
38. The Chemistry of Organic Silicon Compounds (Ed.: S. Patai), Wiley, 1989; M. J. S. Dewar, G. L. Grady, E. F. Healy, Organometallics 1987, 6, 186; M. J. S. Dewar, G. L. Grady, J. P. Stewart, J. Am. Chem. Soc. 1984, 106, 6771.
39. K. D. Dobbs, W. J. Hehre, Organometallics 1986, 5, 2057.
40. Gmelin, Handbook of Inorganic Chemistry (Organogermanium Compounds. Part 1), 8th ed, Springer, 1988.
41. Rücker, D. Lang, J. Sauer, A. Friege, R. Sustmann, Chem. Ber. 1980, 113, 1663.