Proton-induced intra-complex hydride transfer involving bicyclo[2.2.2]octane units as a rigid spacer and as a carbocation precursor

International Journal of Mass Spectrometry

Volumn 228, Issue 2-3, 2003, Pages 321-339

  Matthias, Carsten ^a   Bredenkötter, Björn ^a   Kuck, Dietmar ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Bicyclo 2.2.2 octanes; Hydride transfer; Ion molecule complexes; Metastable ions; Proton transfer; Protonolysis; Skeletal rearrangement; Tert Butylbenzenes

Indexed keywords

ALKANE DERIVATIVE; BICYCLO[2.2.2]OCTANE DERIVATIVE; BUTANE;

ARTICLE; CYCLIZATION; PROTON TRANSPORT; RIGIDITY; SYNTHESIS;

EID: 0043208875     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1387-3806(03)00201-X     Document Type: Article

References (56)

1. A.G. Harrison, Chemical Ionization Mass Spectrometry, 2nd ed., CRC Press, Boca Raton, 1992.
2. Richter W.J., Schwarz H. Angew. Chem. 90:1978;449 Richter W.J., Schwarz H. Angew. Chem. Int. Ed. Engl. 17:1978;424.
3. Richter W.J., Schwarz H. Angew. Chem. 90:1978;449 Richter W.J., Schwarz H. Angew. Chem. Int. Ed. Engl. 17:1978;424.
4. Herman J.A., Harrison A.G. Org. Mass Spectrom. 16:1981;423.
5. (a) Berthomieu D., Audier H.E., Denhez J.P., Monteiro C., Mourgues P. Org. Mass Spectrom. 26:1991;271 (b) Berthomieu D., Audier H.E., Monteiro C., Denhez J.P. Rapid Commun. Mass Spectrom. 5:1991;415 For reviews on protonated alkylbenzenes and H/D scrambling, see:
6. (a) Berthomieu D., Audier H.E., Denhez J.P., Monteiro C., Mourgues P. Org. Mass Spectrom. 26:1991;271 (b) Berthomieu D., Audier H.E., Monteiro C., Denhez J.P. Rapid Commun. Mass Spectrom. 5:1991;415 For reviews on protonated alkylbenzenes and H/D scrambling, see:
7. Kuck D. Mass Spectrom. Rev. 9:1990;583 (b) Kuck D. Int. J. Mass Spectrom. 213:2002;101.
8. Kuck D. Mass Spectrom. Rev. 9:1990;583 (b) Kuck D. Int. J. Mass Spectrom. 213:2002;101.
9. Berthomieu D., Brenner V., Ohanessian G., Denhez J.P., Millié P., Audier H.E. J. Phys. Chem. 99:1995;712 (b) Audier H.E., Monteiro C., Mourgues P., Berthomieu D. Org. Mass Spectrom. 25:1990;245.
10. Berthomieu D., Brenner V., Ohanessian G., Denhez J.P., Millié P., Audier H.E. J. Phys. Chem. 99:1995;712 (b) Audier H.E., Monteiro C., Mourgues P., Berthomieu D. Org. Mass Spectrom. 25:1990;245.
11. Kuck D., Matthias C. J. Am. Chem. Soc. 114:1992;1901.
12. Denhez J.P., Audier H.E., Berthomieu D. Rapid Commun. Mass Spectrom. 9:1995;1210.
13. Kuck D., Schneider J., Grützmacher H.F. J. Chem. Soc. Perkin Trans. II:1985;689.
14. Mormann M., Kuck D. Int. J. Mass Spectrom. 219:2002;497.
15. Munson M.S.B., Field F.H. J. Am. Chem. Soc. 89:1967;1047.
16. Harrison A.G., Lin P.H., Leung H.W. Adv. Mass Spectrom. 7B:1978;1394.
17. Wesdemiotis C., Schwarz H., van de Sande C.C., van Gaever F. Z. Naturforsch. 34b:1979;495.
18. Fornarini S. Mass Spectrom. Rev. 15:1996;365.
19. Fornarini S., Crestoni M.E. Acc. Chem. Res. 31:1998;827.
20. Kuck D., Bäther W., Grützmacher H.-F. J. Am. Chem. Soc. 101:1979;7154.
21. Matthias C., Kuck D. Org. Mass Spectrom. 28:1993;1073.
22. Matthias C., Weniger K., Kuck D. Eur. Mass Spectrom. 1:1995;445.
23. Matthias C., Anlauf S., Weniger K., Kuck D. Int. J. Mass Spectrom. 199:2000;155.
24. Matthias C., Kuck D. Int. J. Mass Spectrom. 217:2002;131.
25. (a) Heidrich D. Angew. Chem. 114:2002;3343 (b) Heidrich D. Angew. Chem. Int. Ed. Engl. 41:2002;3208.
26. (a) Heidrich D. Angew. Chem. 114:2002;3343 (b) Heidrich D. Angew. Chem. Int. Ed. Engl. 41:2002;3208.
27. Filippi A., Roselli G., Renzi G., Grandinetti F., Speranza M. Chem. Eur. J. 9:2003;2072.
28. Berthomieu D., Brenner V., Ohanessian G., Denhez J.P., Millié P., Audier H.E. J. Am. Chem. Soc. 115:1993;2505.
29. Ma J.C., Dougherty D.A. Chem. Rev. 97:1997;1303.
30. Denhez J.P., Audier H.E., Berthomieu D. Org. Mass Spectrom. 28:1993;704.
31. Cacace F., Crestoni M.E., Fornarini S., Kuck D. J. Am. Chem. Soc. 115:1993;1024 For the effect of cis- and trans-1,4-diyl spacers, see:
32. Kuck D., Thölmann D., Grützmacher H.F. J. Chem. Soc. Perkin Trans. 2:1990;251.
33. Crestoni M.E., Fornarini S., Kuck D. J. Phys. Chem. 99:1995;3150.
34. Meot-Ner (Mautner) M., Hamlet P., Hunter E.P., Field F.H. J. Am. Chem. Soc. 100:1978;5466.
35. Hunter E.P.L., Lias S.G. J. Phys. Chem. Ref. Data. 27:1998;413.
36. Mandelbaum A. Adv. Mass Spectrom. 13:1994;227.
37. D. Kuck, manuscript in preparation.
38. P. Vogel, Carbocation Chemistry, Elsevier, Amsterdam, 1985.
39. (a) M.E. Crestoni, S. Fornarini, M. Lentini, M. Speranza, J. Chem. Soc. Chem. Commun. (1995) 121 (b) Crestoni M.E., Fornarini S., Lentini M., Speranza M. J. Phys. Chem. 100:1996;8285.
40. (a) M.E. Crestoni, S. Fornarini, M. Lentini, M. Speranza, J. Chem. Soc. Chem. Commun. (1995) 121 (b) Crestoni M.E., Fornarini S., Lentini M., Speranza M. J. Phys. Chem. 100:1996;8285.
41. Ausloos P., Lias S.G. J. Am. Chem. Soc. 92:1970;5037.
42. Mormann M., Kuck D. J. Mass Spectrom. 34:1999;384.
43. Mormann M., Kuck D. Int. J. Mass Spectrom. 210/211:2001;531.
44. Kuck D. Int. J. Mass Spectrom. Ion Process. 117:1992;441.
45. (a) Wesdemiotis C., Schilling M., Schwarz H. Angew. Chem. 91:1979;1017 (b) Wesdemiotis C., Schilling M., Schwarz H. Angew. Chem. Int. Ed. Engl. 18:1979;950.
46. (a) Wesdemiotis C., Schilling M., Schwarz H. Angew. Chem. 91:1979;1017 (b) Wesdemiotis C., Schilling M., Schwarz H. Angew. Chem. Int. Ed. Engl. 18:1979;950.
47. (a) Houriet R., Schwarz H. Angew. Chem. 91:1979;1018 (b) Houriet R., Schwarz H. Angew. Chem. Int. Ed. Engl. 18:1979;951.
48. (a) Houriet R., Schwarz H. Angew. Chem. 91:1979;1018 (b) Houriet R., Schwarz H. Angew. Chem. Int. Ed. Engl. 18:1979;951.
49. Schwarz H., Reetz M.T., Maier W.F., Wesdemiotis C., Chatziiosifides I., Schilling M. Angew. Chem. 91:1979;1019 Schwarz H., Reetz M.T., Maier W.F., Wesdemiotis C., Chatziiosifides I., Schilling M. Angew. Chem. Int. Ed. Engl. 18:1979;952.
50. Schwarz H., Reetz M.T., Maier W.F., Wesdemiotis C., Chatziiosifides I., Schilling M. Angew. Chem. 91:1979;1019 Schwarz H., Reetz M.T., Maier W.F., Wesdemiotis C., Chatziiosifides I., Schilling M. Angew. Chem. Int. Ed. Engl. 18:1979;952.
51. C. Matthias, D. Kuck, unpublished results See C. Matthias, Doctoral thesis, Universität Bielefeld, 1996.
52. C. Matthias, D. Kuck, unpublished results See C. Matthias, Doctoral thesis, Universität Bielefeld, 1996.
53. Roberts J.D., Moreland W.T. Jr., Frazer W. J. Am. Chem. Soc. 75:1953;637.
54. Fiandanese V., Marchese G., Martina V., Ronzini L. Tetrahedron Lett. 25:1984;4805.
55. Dewar M.J.S., Goldberg R.S. J. Am. Chem. Soc. 92:1970;1582.
56. Kauer J.C., Benson R.E., Parshall G.W. J. Org. Chem. 30:1965;1431.