3,3-Dichloroprop-2-ene iminium salts (vinylogous Viehe salts): A study of their reactivity towards nucleophiles

Synthesis

Volumn , Issue 5, 1997, Pages 573-588

  Jahn, Ullrich ^a   Andersch, Jens ^a   Schroth, Werner ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PROPYLENE;

ALKYLATION; ARTICLE; COMPLEX FORMATION; COVALENT BOND; DRUG SYNTHESIS; KINETICS; PROTEIN ASSEMBLY;

EID: 0031010466     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1221     Document Type: Article

References (38)

1. Schroth, W.; Jahn, U.; Ströhl, D. Chem. Ber. 1994, 127, 2013.
2. Viehe, H.G. In Advances in Organic Chemistry Vol. 9, Iminium Salts in Organic Chemistry Taylor, E. C., Ed.; Wiley: New York, Part 1, 1976; pp 343-419.
3. Liebscher, J.; Hartmann, H. Synthesis 1979, 241.
4. Pohland, A. E.; Benson, W. R. Chem. Rev. 1966, 66, 161.
5. Pulst, M.; Weissenfels, M. Z. Chem. 1974, 16, 337.
6. Roedig, A.; Manger, R.; Schödel, S. Chem. Ber. 1960, 93, 2294 and literature cited therein.
7. Zakharkin, L. I.; Sorokina, L. P. Izv. Akad. Nauk SSSR. Ser. Khim. 1962, 287 and literature cited therein.
8. Julia, M.; Bullot, J. Bull. Soc. Chim. Fr. 1959, 1828.
9. Märkl, G.; Fuchs, R. Tetrahedron Lett. 1972, 4691.
10. Schroth, W.; Spitzner, R.; Hugo, S. Synthesis 1982, 199.
11. Schroth, W.; Spitzner, R.; Koch, B. Synthesis 1982, 203.
12. Spitzner, R.; Menzel, M.; Schroth, W. Synthesis 1982, 206.
13. We are indebted to Dr. H. D. Schädler for the calculations performed with the program MOPAC, QCPE (Indiana University, Bloomington).
14. A comparable situation arises for B (R = Me, R′ = R″ = H) and also for the N,N-dimethyl propene iminium cation. Analogous results are also obtained by both MNDO and ab initio calculations for the propyne iminium ion: Maas, G.; Würthwein, E.-U.; Singer, B.; Mayer, T.; Krauss, D. Chem. Ber. 1989, 122, 2311.
15. More details in: Ph. D. Thesis, Jahn, U., Universität Halle, Germany, 1992.
16. Hanack, M.; Korhummel, C. Synthesis 1987, 944-947, especially p 945.
17. Similarly produced from 4: Dziadulewicz, E. E.; Giles, M.; Moss, W. O.; Gallagher, T.; Harman, M.; Hursthouse, M. B. J. Chem. Soc., Perkin Trans. I 1989, 1793.
18. Preparation of 13, R′ = aryl, from 4 see: Schroth, W.; Burkhardt, U.; Thieß, P.; Spitzner, R. Z. Chem. 1984, 435.
19. On this principle see: Schroth W.: "1,3-Thiazines and related systems, promising fields in heterocyclic chemistry". In: Studies in Organic Chemistry 35, Chemistry of Heterocyclic Compounds Kovác J.; Zálupsky P., Ed.; Elsevier: Amsterdam, 1988, pp 115-131.
20. Kleinpeter, E.; Schroth, W. Phosphorus Sulfur Silicon Relat. Elem. 1990, 47, 427. Kleinpeter, E.; Schroth, W.; Pihlaja, K. Magn. Reson. Chem. 1991, 29, 223.
21. Kleinpeter, E.; Schroth, W. Phosphorus Sulfur Silicon Relat. Elem. 1990, 47, 427. Kleinpeter, E.; Schroth, W.; Pihlaja, K. Magn. Reson. Chem. 1991, 29, 223.
22. Dudinov, A. A.; Belenkii, L. I.; Krayushkin, M. M. Khim. Geterotsikl. Soedin. 1990, 42.
23. Groß, H.; Gloede, J.; Kunath, D. Tetrahedron Lett. 1967, 4089. Knoll, F.; Krumm, U. Chem. Ber. 1971, 104. 31.
24. Groß, H.; Gloede, J.; Kunath, D. Tetrahedron Lett. 1967, 4089. Knoll, F.; Krumm, U. Chem. Ber. 1971, 104. 31.
25. Schneider. P.; Fischer, G. W. J. Prakt. Chem. 1980, 322, 229 and literature cited therein.
26. Preparation of 27a also by Vilsmeier reaction of the corresponding substituted acetophenone: Arnold, Z.; Holy, A. Collect. Czech. Chem. Commun. 1963, 28, 869.
27. Alternative synthesis: Davtyan, N. M.; Martirosyan, G. T.; Babayan, A. T. Zh. Org. Khim. 1968, 4, 556.
28. Sorokina, L. P.; Zakharkin, L. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1964, 73.
29. Crombie, L.; Eskins, M.; Games, D. E.; Louder, C. J. Chem. Soc., Perkin Trans. I 1979, 478.
30. Liebscher, J.; Hartmann, H. J. Prakt. Chem. 1976, 318, 705.
31. Pochat, F.; Levas, E. C. R. Acad. Sci. Ser. C 1971, 273, 382.
32. Pochat, F.; Levas, E. Bull. Soc. Chim. Fr. 1972, 3145.
33. Nesmeyanov, A. N.; Freidlina, R. Kh.; Zakharkin, L. I. Dokl. Akad. Nauk SSSR 1954, 97, 91.
34. Glass, R. S. J. Organomet. Chem. 1973, 61, 83.
35. Schroth, W.; Andersch, J.; Schädler, H.-D.; Spitzner, R. Chem.-Ztg. 1989, 113, 261.
36. Holy, A.; Krupizka, J.; Arnold, Z. Collect. Czech. Chem. Commun. 1965, 30, 4127.
37. Cf.: McKenna, C. M.; Higa, M. T.; Cheung, N. H.; McKenna, M.-C. Tetrahedron Lett. 1977, 155.
38. Zakharkin, L. I.; Sorokina, L. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1958, 1445.