Charge-transfer absorption of olefins with nitrosonium. structural relevance to the dimethylbutene complex with dinitrogen tetraoxide

Research on Chemical Intermediates

Volumn 22, Issue 3, 1996, Pages 209-224

  Bosch, Eric ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542587138     PISSN: 09226168     EISSN: None     Source Type: Journal    
DOI: 10.1163/156856796X00412     Document Type: Article

References (55)

1. a) H. Shechter, Rec. Chem Prog. 25, 55 (1964).
2. b) H.O. Larson. In: The Chemistry of the Nitro and Nitroso Groups, H. Feuer (Ed), Interscience, New York, 1969, pp. 319 ff.
3. a) W.A. Pryor, J.W. Lightsey, and D.F. Church, J Am. Chem Soc. 104, 6685 (1982)
4. b) D.H. Giamalva, G.B. Kenion, D.F. Church, and W.A. Pryor, J. Am. Chem Soc. 109, 7059 (1987).
5. J. Chatterjee, R.G. Coombes, J.R. Barnes, and M.J. Fildes, J. Chem Soc., Perkin Trans 1, 1031 (1995).
6. a) T.F. Redmond and B.B. Wayland, J. Phys. Chem. 72, 1626 (1968)
7. b) D.W. James and R C. Marshall, J. Phys Chem 72, 2963 (1968).
8. c) J, Brunning, M.J. Frost, and I.W.M. Smith, Int J Chem. Kinet. 20, 957 (1988).
9. d) A.J. Vosper, J. Chem Soc (A), 2191 (1970).
10. See Pryor et al. in Ref 2.
11. a) E.F. Schoenbrunn and J.H. Gardner, J. Am. Chem. Soc. 82, 4905 (1960).
12. b) B.T. Ustavshchikov, V.A. Podgornova, N.V. Dormidontova, and M.I. Farberov, Dokl. Akad Nauk SSSR 157, 143 (1964).
13. J.B. Wilkes and R.G. Wall, J Org Chem. 45, 247 (1980).
14. L. Parts and J.T. Miller, Jr. J. Phys. Chem. 73, 3088 (1969).
15. L. Parts and J.T. Miller, Jr. J. Chem Phys. 43, 136 (1965).
16. A. Givan and A. Loewenschuss, J. Chem. Phys. 94, 7562 (1991).
17. a) M. Nakata and H. Frei, J. Phys. Chem. 93, 7670 (1989).
18. b) M. Nakata and H. Frei, J. Am. Chem. Soc 111, 5240 (1989).
19. c) M. Nakata, K. Shibuya, and H. Frei, J. Phys. Chem. 94, 8168 (1990).
20. a) D.J. Fitzmaurice and H. Frei, J. Phys. Chem 95, 2652 (1991).
21. b) M. Nakata and H. Frei, J. Am. Chem Soc. 114, 1363 (1992).
22. c) D.J. Fitzmaurice and H. Frei, J. Phys. Chem 96, 10308 (1992). See also: H. Frei, Chimia 45, 175 (1991).
23. c) D.J. Fitzmaurice and H. Frei, J. Phys. Chem 96, 10308 (1992). See also: H. Frei, Chimia 45, 175 (1991).
24. d) M. Nakata, Spectrochim Acta 50A, 1455 (1994).
25. e) J.C. Loison, C. Dedonder-Lardeux, C. Jouvet, and D. Solgadi, J. Phys. Chem. 95, 9192 (1991).
26. F. Blatter and H. Frei, J. Phys Chem. 97, 1178 (1993).
27. E. Bosch and J.K. Kochi, Res. Chem Intermed. 19, 811 (1993).
28. a) M.L. Scheinbaum and M.B. Dines, Tetrahedron Lett. 2205 (1971).
29. b) G.H. Lee, J.M. Lee, W.B. Jeong, and K. Kim, Tetrahedron Lett 29, 4437 (1988).
30. c) G.A. Olah, P. Schilling, P.W. Westerman, and H.C. Lin, J. Am. Chem. Soc. 96, 3581 (1974).
31. E. Iglesias, L. Garcia-Rio, J.R. Leis, M.E. Pena, and D.L.H. Williams, J. Chem. Soc , Perkin Trans. 2, 1673 (1992).
32. + from octyl nitrite with trifluoroacetic acid, see Iglesias et al. in Ref. 16.
33. Y. Tapuhi and E. Grushka. In: The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives, S. Patai (Ed.), Wiley, New York, 1982, Supplement F, Part 2, p. 909.
34. D.I. Makhonkov, A.V. Cheprakov, M.A. Rodkin, and I.P. Beletskaya, Zh. Org. Khim. 24, 241 (1988).
35. a) S. Brownstein, E. Gabe, F. Lee, and L. Tan, J Chem. Soc., Chem. Commun. 1567 (1984).
36. b) S. Brownstein, E. Gabe, F. Lee, and A. Piotrowski, Can J. Chem. 64, 1661 (1986).
37. E. Bosch and J.K. Kochi, J. Org. Chem. 59, 3314 (1994).
38. R. Foster, Organic Change-Transfer Complexes, Academic, New York, 1969.
39. E.K. Kim and J.K. Kochi, J Am. Chem. Soc 113, 4962 (1991).
40. R.M Minyaev, M.E. Kletskii, and V.I. Minkin, Zh. Org. Khim. 23, 2508 (1987).
41. S.G. Lias, Chem. Phys. Lett. 54, 147 (1978).
42. a) E. Bosch and J.K. Kochi, J Org Chem. 60, 3172 (1995).
43. b) S. Ricard, P. Audet, and R. Savoie, J Molec Struct 178, 135 (1988).
44. M. Tsuchiya, R. Akaba, S. Aihara, H. Sakuragi, and K. Tokumaru, Chem Lett. 1727 (1986).
45. a) R.S. Mulliken, J. Am. Chem Soc 72, 600 (1950).
46. b) R.S. Mulliken and W.B. Person, Molecular Complexes, Wiley, New York, 1969.
47. M.W. Hanna and J.L. Lippert. In: Molecular Complexes, Vol. 1, R. Foster (Ed.), Crane Russak, New York, 1973, p. 2 ff.
48. T.M. Bockman, Z. Karpinski, S. Sankararaman, and J.K. Kochi, J. Am. Chem Soc. 114, 1970 (1992).
49. E. Bosch and J.K. Kochi, submitted for publication. See also M. Nakata, in Ref. 12 d)
50. K.Y. Lee and J.K. Kochi, J. Chem Soc , Perkin Trans 2, 237 (1994).
51. a) C.C. Addison and D. Sutton, Prog Inorg. Chem 8, 195 (1967).
52. b) C.C. Addison, Chemistry in Liquid Dinitrogen Tetroxide, Vieweg, Braunschweig, 1967.
53. W.A. Noyes, Org Syntheses Coll Vol. 2, 2, 108 (1961)
54. J.R Morton and H.W. Wilcox, Inorg Synth. 4, 48 (1953).
55. E.W. Meijer and H. Wynberg, J. Chem. Ed 59, 1071 (1982).