Prototropy in the System - ClCH-N = N-; Cycloadditions of 1-Aza-2-azoniaallene Cations Derived from Aldehydes

Synthesis

Volumn , Issue 2, 1996, Pages 274-280

  Guo, Yiping ^a   Wang, Quanrui ^b   Jochims, Johannes C ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029987066     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4189     Document Type: Article

References (36)

1. Moon, M. W. J. Org. Chem. 1972, 37, 383.
2. Moon, M. W. J. Org. Chem. 1972, 37, 386.
3. Moon, M. W. J. Org. Chem. 1972, 37, 2005.
4. Wang, Q.; Jochims, J. C.; Köhlbrandt, S.; Dahlenburg, L.; Al-Talib, M.; Hamed, A.; Ismail, A. Synthesis 1992, 710.
5. Wang, Q.; Al-Talib, M.; Jochims, J. C. Chem. Ber. 1994, 127, 541.
6. Wang, Q.; Amer, A.; Mohr, S.; Ertel, E.; Jochims, J. C. Tetrahedron 1993, 49, 9973.
7. Wang, Q.; Mohr, S.; Jochims, J. C. Chem. Ber. 1994, 127, 947.
8. Wang, Q.; Amer, A.; Troll, C.; Fischer, H.; Jochims, J. C. Chem. Ber. 1993, 126, 2519.
9. Gstach, H. Seil, P. Synthesis 1990, 803.
10. Gstach, H. Seil, P. Synthesis 1990, 808.
11. Gstach, H. Seil, P. Synthesis 1990, 1048.
12. Majchrzak, M. W.; Jefferson, E. A.; Warkentin, J. J. Am. Chem. Soc. 1990, 112, 2449.
13. Jefferson, E. A.; Warkentin, J. J. Org. Chem. 1994, 59, 455.
14. Jiao, H.; Schleyer, P. v. R. J. Chem. Soc., Faraday Trans. 1994, 90, 1559.
15. Kroemer, R. T.; Gstach, H.; Liedl, K. R.; Rode, B. M. J. Am. Chem. Soc. 1994, 116, 6277.
16. Kroemer, R. T.; Gstach, H.; Liedl, K. R.; Rode, B. M. J. Chem. Soc., Perkin Trans 2 1994, 16, 2129.
17. Tronchet, J. M. J.; Baehler, B.; Le-Hong, N.; Livio, P. F. Helv. Chim. Acta 1971, 54, 921.
18. Hegarty, A. F.; O'Mahony, T. A. F.; Quain, P.; Scott, F. L. J. Chem. Soc., Perkin Trans. 2 1973, 2047.
19. Hegarty, A. F.; Coy, J. H.; Scott, F. L. J. Chem. Soc., Perkin Trans. 2 1975, 104.
20. Pross, A.; Sternhell, S. Aust. J. Chem. 1971, 24, 1437.
21. For instance: El-Reedy, A. M.; Hussain, S. M.; Youssef, M. M. M. J. Prakt. Chem. 1988, 330, 521.
22. Pechmann, H. v. Ber. Dtsch. Chem. Ges. 1894, 27, 320.
23. Pechmann, H. v.; Seeberger, L. Ber. Dtsch. Chem. Ges. 1894, 27, 2121.
24. Huisgen, R.; Seidel, M.; Wallbillich, G.; Knupfer, H. Tetrahedron 1962, 17, 3.
25. Kaugars, G. US Patent, 3745215; Chem. Abstr. 1973, 79, 78412.
26. Kaugars, G. US Patent, 3870505; Chem. Abstr. 1975, 83, 78891.
27. Padwa, A.; Nahm, S. J. Org. Chem. 1981, 46, 1402.
28. Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; Wiley: New York 1984, p291 ff.
29. Nachbaur, E.; Faleschini, G. In Houben-Weyl, 4th ed, Vol. E8d; Schaumann, E., Ed.; Thieme: Stuttgart 1994; p479 ff.
30. Elguero, J. In Comprehensive Heterocyclic Chemistry, Vol. 5; Katritzky, A. R.; Rees, C. W.; Potts, K. T., Eds.; Pergamon: Oxford, 1984; p167 ff.
31. Tomilov, Y. V.; Okonnishnikova, G. P.; Shulishov, E. V.; Nefedov, O. M. Mendeleev Commun. 1994, 119.
32. A Wagner-Meerwein rearrangement is defined as a migration of a C-substituent to a vicinal carbocation center. In our cases, migration of a C- or H-substituent occurs to an electron deficient vicinal nitrogen atom. The term 'generalized Wagner-Meerwein rearrangement' means that similar mechanisms are operative in both cases.
33. Wirschun, W.; Fischer, H.; Jochims, J. C., unpublished work.
34. Anet, F. A. L.; Lee, H. H.; Sudmeier, J. L. J. Am. Chem. Soc. 1967, 59, 4431.
35. Baldwin, J. E.; Adlington, R. M.; Bottaro, J. C.; Kolhe, J. N.; Perry, M. W. D.; Jain, A. U. Tetrahedron 1986, 42, 4223.
36. Minz, M. J.; Walling, C. Org. Synth. Coll. Vol. V: Wiley: New York 1973; p 184.