A novel dimerization mode of a cyclic ketene imine

Chemistry - A European Journal

Volumn 10, Issue 17, 2004, Pages 4353-4357

  Langhals, Elke ^a   Huisgen, Rolf ^a   Polborn, Kurt ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Base catalysis; Cycloaddition; Dimerization; Heterocycles; Ketene imines

Indexed keywords

CATALYSIS; DIMERIZATION; FLUORINE COMPOUNDS; PROTONS; X RAY ANALYSIS;

IONIC CHAIN REACTION; KETENE IMINE; THIOIMIDATE GROUP;

ACETONITRILE;

ACETONITRILE; BASE; CARBONYL DERIVATIVE; CYCLOALKENE; DIMER; FLUORINE DERIVATIVE; IMINE; KETENE DERIVATIVE; NITRILE; POTASSIUM CYANIDE; THIOIMIDE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; DIMERIZATION; ION TRANSPORT; QUANTUM YIELD; RING OPENING; ROOM TEMPERATURE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 4644225350     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400264     Document Type: Article

References (34)

1. C. L. Stevens, J. C. French, J. Am. Chem. Soc. 1954, 76, 4398-4402.
2. M. W. Barker, J. D. Rosamond, J. Heterocycl. Chem. 1972, 9, 1147-1148.
3. N. P. Gambaryan, Russ. Chem. Rev. 1976, 45, 630-638.
4. P. D. Del'tsova, N. P. Gambaryan, Y. P. Zeifman, I. L. Knunyants, Russ. J. Org. Chem. 1972, 8, 864-868.
5. N. P. Gambaryan, E. A. Avetisyan, Izv. Akad. Nauk Am. SSR, Khim. Nauki 1978, 358-363.
6. G. G. Furin, V. G. Kiriyanko, E. L. Zhuzhgov, Russ. J. Org. Chem. 2000, 36, 24-29; G. G. Furin, V. A. Lopyrev, E. L. Zhuzhgov, N. I. Protsuk, Russ. J. Org. Chem. 2000, 36, 99-104.
7. G. G. Furin, V. G. Kiriyanko, E. L. Zhuzhgov, Russ. J. Org. Chem. 2000, 36, 24-29; G. G. Furin, V. A. Lopyrev, E. L. Zhuzhgov, N. I. Protsuk, Russ. J. Org. Chem. 2000, 36, 99-104.
8. R. Huisgen, E. Langhals, H. Nöth, J. Org. Chem. 1990, 55, 1412-1414.
9. R. Huisgen, G. Mloston, E. Langhals, T. Oshima, Helv. Chim. Acta 2002, 85, 2668-2685.
10. R. Huisgen, E. Langhals, K. Polborn, K. Karaghiosoff, Helv. Chim. Acta 2004, 87, 1426-1445.
11. R. Huisgen in Chemistry and Biological Application of Oxygen- and Sulfur-Containing Heterocycles (Ed.: V. G. Kartsev), IBS Press, Moscow, 2003, pp. 83-101.
12. H. Giera, R. Huisgen, E. Langhals, K. Polborn, Helv. Chim. Acta 2002, 85, 1523-1545.
13. J. L. Carlos, R. K. Karl, S. H. Bauer, J. Chem. Soc. Farad. Trans. 2 1974, 70, 177-187; V. W. Laurie, D. T. Pence, J. Chem. Phys. 1963, 38, 2693-2697.
14. J. L. Carlos, R. K. Karl, S. H. Bauer, J. Chem. Soc. Farad. Trans. 2 1974, 70, 177-187; V. W. Laurie, D. T. Pence, J. Chem. Phys. 1963, 38, 2693-2697.
15. B. E. Smart in "Fluorinated Organic Molecules" in Molecular Structure and Energetics, Vol. 3 (Eds.: J. F. Liebman, A. Greenberg), VCH Weinheim, 1986, pp. 141-191.
16. R. Knorr, K. Ferchland, J. Mehlstäubl, T. P. Hoang, P. Böhrer, H.-D. Lüdemann, E. Lang, Chem. Ber. 1992, 125, 2041-2049; R. Knorr, J. Ruhdorfer, J. Mehlstäubl, P. Böhrer, D. S. Stephenson, Chem. Ber. 1993, 126, 747-754.
17. R. Knorr, K. Ferchland, J. Mehlstäubl, T. P. Hoang, P. Böhrer, H.-D. Lüdemann, E. Lang, Chem. Ber. 1992, 125, 2041-2049; R. Knorr, J. Ruhdorfer, J. Mehlstäubl, P. Böhrer, D. S. Stephenson, Chem. Ber. 1993, 126, 747-754.
18. F. B. Mallory, C. W. Mallory in Encyclopedia of Nuclear Magnetic Resonance, Vol. 3 (Eds.: D. M. Grant, R. K. Harris), Wiley, 1996, pp. 1491-1501.
19. C. J. Jameson in Multinuclear NMR (Ed.: J. Mason), Plenum Press, New York, 1987, pp. 437-446; J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 113-115 and J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 421-446.
20. C. J. Jameson in Multinuclear NMR (Ed.: J. Mason), Plenum Press, New York, 1987, pp. 437-446; J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 113-115 and J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 421-446.
21. C. J. Jameson in Multinuclear NMR (Ed.: J. Mason), Plenum Press, New York, 1987, pp. 437-446; J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 113-115 and J. W. Emsley, L. Phillips, V. Wray, Progr. NMR Spectrosc. 1977, 10, 421-446.
22. W. S. Brey, K. C. Ramey, J. Chem. Phys. 1963, 39, 844-845; C. G. Moreland, W. S. Brey, J. Chem. Phys. 1966, 45, 803-808. B. C. Anderson, J. Org. Chem. 1968, 33, 1016-1018.
23. W. S. Brey, K. C. Ramey, J. Chem. Phys. 1963, 39, 844-845; C. G. Moreland, W. S. Brey, J. Chem. Phys. 1966, 45, 803-808. B. C. Anderson, J. Org. Chem. 1968, 33, 1016-1018.
24. W. S. Brey, K. C. Ramey, J. Chem. Phys. 1963, 39, 844-845; C. G. Moreland, W. S. Brey, J. Chem. Phys. 1966, 45, 803-808. B. C. Anderson, J. Org. Chem. 1968, 33, 1016-1018.
25. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463.
26. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, Chem. Commun. 1968, 723-724; F. Hibbert, K. P. P. Hunte, J. Chem. Soc. Perkin 2 1983, 1895-1899.
27. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, Chem. Commun. 1968, 723-724; F. Hibbert, K. P. P. Hunte, J. Chem. Soc. Perkin 2 1983, 1895-1899.
28. L. A. Kurasov, A. F. Pozharskii, V. V. Kuz'menko, Russ. J. Org. Chem. 1983, 19, 759-763.
29. J. F. Coetzee, G. R. Padmanabhan, J. Phys. Chem. 1965, 69, 3193-3196; J. F. Coetzee, Prog. Phys. Org. Chem. 1967, 4, 45-92.
30. J. F. Coetzee, G. R. Padmanabhan, J. Phys. Chem. 1965, 69, 3193-3196; J. F. Coetzee, Prog. Phys. Org. Chem. 1967, 4, 45-92.
31. I. F. Tupitsyn, A. S. Popov, Russ. J. Gen. Chem. 2001, 71, 89-101.
32. R. Huisgen, G. Mloston, K. Polborn, R. Sustmann, Chem. Eur. J. 2003, 9, 2256-2263.
33. G. M. Sheldrick, Programs for the Solution and Refinement of Crystal Structures, University of Göttingen, 1986 and 1993.
34. L. Zsolnai, G. Huttner, Program ZORTEP, University of Heidelberg, 1994.