In search of the spin-delocalization effect from the correlation analysis of relative rates of the trichloromethyl-bromo-addition reactions to fourteen p-Y-substituted phenylacetylenes

Tetrahedron

Volumn 52, Issue 8, 1996, Pages 3017-3028

  Jiang, Xi Kui ^a   Ji, Guo Zhen ^a   Xie, John Rong Yuan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030027228     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00021-X     Document Type: Article

References (46)

1. a) Jiang, X. -K.; Ji, G.-Z. J. Org. Chem. 1992, 57, 6051-6056 and references cited therein.
2. b) Viehe, H. G.; Janousek, Z.; Merenyi, R. Substituent Effects in Radical Chemistry; Reidel: Dordrecht, 1986.
3. c) Arnold, D. R. in Ref. 1b; pp 171-188.
4. a) Guo, G.H.-X.; Sun, S. S.-X.; Ji, G.-Z.; Jiang, X.-K. J. Chem. Res. (S) 1 993, 166-167; (M) 1993, 1123-1143.
5. a) Guo, G.H.-X.; Sun, S. S.-X.; Ji, G.-Z.; Jiang, X.-K. J. Chem. Res. (S) 1 993, 166-167; (M) 1993, 1123-1143.
6. b) Jiang, X.-K.; Liu, W. W.-Z.; Wu, S.-H. J. Phys. Org. Chem. 1994, 7, 96-104.
7. c) Jiang, X.-K.; Liu, W. W.-Z.; Wu, S.-H. Tetrahedron 1994, 50, 7503-7512.
8. d) Jiang, X.-K.; Ji, G.-Z.; Wang, D. Z.-R.; Xie, J. R.-Y. J. Phys. Org. Chem. 1995, 8, in press.
9. e) Zhang, Y.-H.; Jiang, B.; Zhou, C.-M.; Jiang, X.-K. Chin. J. Chem. 1994, 12, 516-523.
10. f) Zhang, Y.-H.; Guo, G. H-X.; Jin, X.-S.; Jiang, B.-B.; Fu, Y.-H.; Jiang, X.-K. J. Photochemistry and Photobiology (Chem. Section) 1995, 88, 11-14.
11. g) Jiang, X.-K.; Ji, G.-Z.; Wang, D. Z.-R. J. Phys. Org. Chem. 1995, 8, 143-148.
12. h) Jiang, X.-K.; Ji, G.-Z.; Xie, J. R.-Y. J. Chem. Res. (S) 1995, 422-423.
13. i) Zhang, Y.-H.; Ding, W. F.-X.; Zhou, C.-M.; Chen, J.-F.; Jiang, X.-K. J. Chem. Res. (S) accepted.
14. a) Da Silva Correa, C. M. M.; Fleming, M. D. C. M. J. Chem. Soc. Perkin Trans. II 1987, 103-107.
15. b) Ito, O.; Fleming, M. D. C. M. J. Chem. Soc. Perkin Trans. II 1989, 689-693.
16. c) Griesbanm, K., Oswald, A. A.; Hudson, B.E. Jr. J. Am. Chem. Soc. 1963, 85, 1969-1974.
17. a) Huang, W.-Y.; Wang, W; Huang, B.N. Acta chim. Sin. 1985, 43, 409-410; 1986, 44, 45-50.
18. a) Huang, W.-Y.; Wang, W; Huang, B.N. Acta chim. Sin. 1985, 43, 409-410; 1986, 44, 45-50.
19. b) Huang, W.-Y.; Chen, J.-L. Acta Chim. Sin 1987, 45, 445-449; Engl. Ed. 1986, 381-386.
20. b) Huang, W.-Y.; Chen, J.-L. Acta Chim. Sin 1987, 45, 445-449; Engl. Ed. 1986, 381-386.
21. a) Brandsma, L. Studies in Organic Chemistry 34 Preparative Acetylenic Chemistry (2nd Ed.), Elsevier Amsterdam, 1988; pp. 159-170.
22. b) Berliner, E. in Organic Reactions, Vol. 5; R. Adams Ed.; Wiley: New York, 1949; pp. 254-263.
23. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280-2286.
24. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
25. Dieck., H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259-263.
26. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282-284.
27. Otto, M. M. J. Am. Chem. Soc. 1934, 56, 1393-1394.
28. Bott, R. W.; Eaborn, C.; Walton, D. R. M. J. Chem. Soc. 1965, 384-388.
29. Dawson, D. A.; Reynolds, W. F. Can. J. Chem. 1975, 53, 373-382.
30. Allen, A. D.; Cook, C. D. Can. J. Chem. 1963, 41, 1084-1087.
31. Eaborn, C.; Thompson, A. R.; Walton, D. R. M. J. Chem. Soc. (C). 1967, 1364-1366.
32. a) Skell, S. P.; Garner, A. Y. J. Am. Chem. Soc. 1956, 78, 5430-5433.
33. b) Russell, G. A. in Investigation of Rates and Mechanisms of Reactions; Friess, S. L.; Lewis, E. S.; Weissberger, A. Eds.; Interscience: New York, 1961; pp. 343-344.
34. c) Cadogan, J. I. G.; Sadler, I. H. J. Chem. Soc. (B) 1966, 1191-1205.
35. a) Nonhebel, D. C.; Walton, J. C. Free-radical Chemistry. Structure and mechanism; Cambridge University Press: 1974; pp. 128-145.
36. b) Pryor, W. A.; Tang, F. Y.; Tang, R. H.; Church, D. F. J. Am. Chem. Soc. 1982, 104, 2885-2891.
37. c) Ji, G. Z.; Jiang, X. K.; Zhang, Y. H.; Yuan, S. G.; Yu, C. X.; Shi, Y. Q.; Zhang, X. L.; Shi, W. T. J. Phys. Org. Chem. 1990, 3, 643-650.
38. d) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
39. a) Dust, J. M.; Arnold, D. R. J. Am. Chem. Soc. 1983, 105, 1221-1227.
40. b) Wayner, D. D. M.; Arnold, D. R. Can. J. Chem. 1984, 62, 1164-1168; 1985, 63, 2378-2383.
41. b) Wayner, D. D. M.; Arnold, D. R. Can. J. Chem. 1984, 62, 1164-1168; 1985, 63, 2378-2383.
42. c) Creary, X. in Substituent Effects in Radical Chemistry; Viehe, H. G.; Janousek, Z.; Merenyi, R. Eds.; Reidel: Dordrecht, 1986; pp. 245-262.
43. d) Creary, X.; Mehrsheikh-Mohammadi, M. E.; McDonald, S. J. Org. Chem. 1987, 52, 3254-3263.
44. Amiel, Y. in The Chemistry of Functional Groups, Supplement C; Patai, S.; Rappoport, Z. Eds.; John Wiley & Sons: Chichester, 1983; pp. 341-348.
45. a) Morrison, R. T.; Boyd, R. N. Organic Chemistry (6th ed.); Prentice-Hall, Inc.: Englewood Cliffs, 1992; pp.425-440.
46. b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry (2nd ed.); Harper & Row, Publishers: New York, 1981; pp. 19-30, 506-513.