Ion molecule reactions of simple amines with carbonyl compounds in the gas phase. An experimental and theoretical study of enamine formation

Journal of Mass Spectrometry

Volumn 31, Issue 7, 1996, Pages 716-726

  Pykäläinen, Mika ^a   Vainiotalo, Anto ^a   Pakkanen, Tapani A ^a   Vainiotalo, Pirjo ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

ab initio calculations; Enamine formation; Imine formation; Ion molecule reactions; Ketone chemical ionization

Indexed keywords

ACETONE; ALKANONE; AMINE; DIAMINE; KETONE; MONOAMINE; REAGENT;

ARTICLE; CALCULATION; CHEMICAL REACTION; GAS; IONIZATION; MASS SPECTROMETRY; PHASE TRANSITION; PRESSURE; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 0029683154     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-9888(199607)31:7<716::AID-JMS346>3.0.CO;2-V     Document Type: Article

References (41)

1. H. Layer, Chem. Rev. 63, 489 (1963).
2. L. L. Muller and J. Harmer, 1 ,2-Cycloadditions Reactions. Interscience, New York (1967).
3. F. Bernardi, A. Bongini, G. Cainelli, M. A. Robb and G. S. Valli, J. Org. Chem. 58, 750 (1993).
4. O. Desmaele and J. Dangelo, J. Org. Chem. 59, 2292 (1994).
5. G. Bertrand and C. Wentrup, Angew. Chem., Int. Ed. Engl. 33, 527 (1994).
6. V. Alexander, Chem. Rev. 95, 273 (1995).
7. T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper and Row, New York, 1976, Chap. 8.
8. H.-W. Wanzlick and W. Löchel, Chem. Ber. 86, 1463 (1953).
9. H. Krässig, Makromol. Chem. 17, 77 (1955).
10. J. B. Lambert, D. E. Huseland and G. Wang, J. Chem. Soc., Chem. Commun. 657 (1986).
11. R. S. Theobald, in Rodd's Chemistry of Carbon Compounds, Vol. 4, Hetorocyclic Compounds, Part C, edited by Coffey and Ansell, 2nd edn, p. 172. Elsevier, Amsterdam (1986).
12. R. E. Valters and W. Flitsch, Ring-Chain Tautomerism, p. 188. Plenum Press, New York (1985).
13. D. Lloyd, R. H. McDougal and D. R. Marshall, J. Chem. Soc. C 780 (1966).
14. P.-L. Lehtelä, K. Joutsiniemi, M. Ahlgrén, J. Vepsäläinen and P. Vainiotalo, in preparation.
15. A. Maquestiau, R. Flammang and L. Nielsen, Org. Mass Spectrom. 15, 376 (1980).
16. J. C. Tabet and D. Fraisse, Org. Mass Spectrom. 16, 45 (1981).
17. D. J. Burinsky, J. E. Campana and R. G. Cooks, Int. J. Mass Spectrom. Ion Processes 62, 303 (1984).
18. M. Vairamani, K. V. Siva Kumar and R. Viswanadha, Indian J. Chem. 31B, 9 (1992).
19. S. E. Biali, C. Lifshitz, Z. Rappoport, M. Kami and A. Mandelbaum, J. Am. Chem. Soc. 103, 2896 (1981).
20. S. E. Biali, G. Depke, Z. Rappoport and H. Schwarz, J. Am. Chem. Soc. 106, 496 (1984).
21. Y. Apeloig, M. Karni, B. Ciommer, G. Depke, G. Frenking, S. Meyn, J. Schmidt and H. Schwarz, Int. J. Mass Spectrom. Ion Processes 59, 21 (1984).
22. G. Bouchoux, Y. Hoppilliard and R. Houriet, New J. Chem. 11, 225 (1987).
23. J. L. Holmes and F. P. Lossing, J. Am. Chem. Soc. 102, 1591 (1980).
24. D. A. Peake, J. Stanley, C. A. Kingsbury and M. L. Gross, Org. Mass Spectrom. 21, 565 (1986).
25. M. Masur, H.-F. Grützmacher, H. Münster and H. Budzikiewicz, Org. Mass Spectrom. 22, 493 (1987).
26. G. Bouchoux, Mass Spectrom. Rev. 7, 1 (1988).
27. G. Bouchoux, Mass Spectrom. Rev. 7, 203 (1988).
28. K. N. Houk, R. W. Strozier, N. G. Rondan, R. R. Fraser and N. Chuaqui-Offermanns, J. Am. Chem. Soc. 102, 1426 (1980).
29. B. J. Smith and L. Radom, J. Am. Chem. Soc. 114, 36 (1992).
30. K. Lammertsma and B. V. Prasad, J. Am. Chem. Soc. 116, 642 (1994).
31. P. Kofel, M. Allemann, H. P. Kellerhals and K. P. Wanczek, Int. J. Mass Spectrom. Ion Process 65, 97 (1985).
32. M. B. Comisarow, V. Grassi and G. Parisod, Chem. Phys. Lett. 57, 413 (1978).
33. J. B. Lambert, D. E. Huseland and G. Wang, J. Chem. Soc., Chem. Commun. 657 (1986).
34. S. G. Lias, J. E. Bartmess, J. F. Liebman, J. L. Holmes, R. D. Levin and W. G. Mallard, J. Phys. Chem. Ref. Data 17, Suppl. 1 (1988).
35. X. Li and A. G. Harrison, J. Am. Chem. Soc. 115, 6327 (1993).
36. H. Budzikiewicz, Org. Mass Spectrom. 23, 561 (1988).
37. A. Kamar, A. B. Young and R. E. March, Can. J. Chem. 64, 1979 (1986).
38. R. E. March and A. B. Young, Can. J. Chem. 66, 591 (1988).
39. E. P. F. Lee and J. M. Dyke, J. Chem. Soc., Faraday Trans. 88, 2111 (1992).
40. J. W. Larson and T. B. McMahon, J. Am. Chem. Soc. 104, 6255 (1982).
41. R. D. Bowen, Mass Spectrom. Rev. 10, 225 (1991).