Sandmeyer reactions. Part 6. A mechanistic investigation into the reduction and ligand transfer steps of Sandmeyer cyanation

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 6, 2002, Pages 1126-1134

  Hanson, Peter ^a   Rowell, Simon C ^a   Taylor, Alec B ^a   Walton, Paul H ^a   Timms, Allan W ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Great Lakes Fine Chemicals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; FREE RADICALS; NEGATIVE IONS; PH EFFECTS; REACTION KINETICS; REDUCTION;

LIGAND TRANSFER;

AROMATIC HYDROCARBONS;

EID: 0036091891     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b200747a     Document Type: Article

References (55)

1. W.A. Waters J. Chem. Soc. 1942 266.
2. J.K. Kochi J. Am. Chem. Soc. 1957 79 2942.
3. C. Galli J. Chem. Soc., Perkin Trans. 2 1981 1459.
4. C. Galli J. Chem. Soc., Perkin Trans. 2 1982 1139.
5. P. Hanson, J.R. Jones, B.C. Gilbert, A.W. Timms J. Chem. Soc., Perkin Trans. 2 1991 1009.
6. P. Hanson, R.C. Hammond, P.R. Goodacre, J. Purcell, A.W. Timms J. Chem. Soc., Perkin Trans. 2 1994 691.
7. P. Hanson, R.C. Hammond, B.C. Gilbert, A.W. Timms J. Chem. Soc., Perkin Trans. 2 1995 2195.
8. E. Pfeil, O. Velten Justus Liebigs Ann. Chem. 1949 562 163.
9. E. Pfeil, O. Velten Justus Liebigs Ann. Chem. 1949 565 183.
10. W.S. Cowdrey, D.S. Davies J. Chem. Soc. 1949 S48.
11. C. Galli J. Chem. Soc., Perkin Trans. 2 1984 897.
12. S.C. Dickerman, K. Weiss, A.K. Ingberman J. Org. Chem. 1956 21 380.
13. S.C. Dickerman, K. Weiss, A.K. Ingberman J. Am. Chem. Soc. 1957 80 1904.
14. S.C. Dickerman, D.J. DeSouza, N. Jacobson J. Org. Chem. 1969 34 710.
15. C.J. Rondestvedt Org. React. (N.Y.) 1960 11 189.
16. C.J. Rondestvedt Org. React. (N.Y.) 1976 24 225.
17. C. Galli Chem. Rev. 1988 88 765.
18. J.K. Kochi J. Am. Chem Soc. 1956 78 1228.
19. T. Cohen, A.G. Dietz, J.R. Miser J. Org. Chem. 1977 42 2053.
20. M.P. Doyle, J.K. Guy, K.C. Brown, S.N. Mahapatro, C.M. VanZyl, J.C. Pladziewicz J. Am. Chem. Soc. 1987 109 1536.
21. B.C. Gilbert, P. Hanson, J.R. Jones, A.C. Whitwood, A.W. Timms J. Chem. Soc., Perkin Trans. 2 1992 629.
22. D.S. Wulfman The Chemistry of Diazonium and Diazo groups, Part 1, Ed.S. Patai Interscience 1978 293.
23. C.H.R. Rømming, K. Wærstad J. Chem. Soc., Chem. Commun. 1965 299.
24. M.L. Crossley, R.H. Kienle, C.H. Benbrook J. Am. Chem. Soc. 1940 62 1400.
25. T. Ignasiak, J. Susko, B. Ignasiak J. Chem. Soc., Perkin Trans. 1 1975 2123.
26. K. Kurnia, D.E. Giles, P.M. May, P. Singh, G.T. Hefter Talanta 1996 43 2045.
27. C. De Stefano P. Mineo C. Rigano S. Sammartano Ann. Chim. (Rome) 83 The computer program used, ES4ECI, was kindly provided by Professor S. Sammartano.
28. A. Günter, A. Zuberbühler Chemia 1970 24 340.
29. M.L. Crossley, R.H. Kienle, C.H. Benbrook Ind. Eng. Chem. Anal. Ed. 1940 12 216.
30. A. Katagiri, S. Yoshimura, S. Yoshizawa Inorg. Chem. 1981 20 4143.
31. A. Katagiri, S. Yoshimura, S. Yoshizawa Inorg. Chem. 1986 25 2278.
32. P. Hanson, P.W. Lövenich, S.C. Rowell, P.H. Walton, A.W. Timms J. Chem. Soc., Perkin Trans. 2 1999 49.
33. M.T. Beck Pure Appl. Chem. 1987 59 1703.
34. F.A. Cotton and G. Wilkinson Advanced Inorganic Chemistry, 5th Edn., Wiley, New York, 1988 44.
35. R.W. Ramette Inorg. Chem. 1986 25 2481.
36. E. Högfeldt Stability Constants of Metal-ion Complexes, Part A, Inorganic Ligands, IUPAC Chem. Data Ser., No. 21, Pergamon, Oxford, 1983 111.
37. R.D. Cannon Electron Transfer Reactions, Butterworths, London, 1980, p. 257.
38. O.J. Parker, J.H. Espenson J. Am. Chem. Soc. 1969 91 1968.
39. J.C. Scaiano, W.J. Leigh, G. Ferraudi Can.J. Chem. 1984 62 2355.
40. A. Mayouf, L. Lemmetyinen, I. Sychttchikova, J. Koskikallio Int.J. Chem. Kinet. 1992 24 579.
41. T. Cohen, R.J. Lewarchik, J.Z. Tarino J. Am Chem. Soc. 1974 96 7753.
42. P. Hanson, A.B. Taylor, P.H. Walton and A.W. Timms unpublished work.
43. B.S. Furniss, A.J. Hannaford, V. Rogers, P.W. G. Smith and A.R. Tatchell Vogel’s Textbook of Practical Organic Chemistry, 4th Edn., Longman, London, 1979 704.
44. A. Longo, T. Buch Inorg. Chem. 1967 6 556.
45. G.J. Kubas Inorg. Synth. 1990 28 68.
46. T.J. Broxton, J.F. Bunnett, C.H. Paik J. Org. Chem. 1977 42 643.
47. G.A. Olah, J.L. Grant J. Am. Chem. Soc. 1975 97 1546.
48. R.M. Elofson, N. Cyr, J.K. Laidler, K.F. Schultz, F.F. Gadallah Can.J. Chem. 1984 62 92.
49. R.M. Elofson, N. Cyr, J.K. Laidler, K.F. Schultz Tetrahedron Lett. 1984 25 3039.
50. C. Kappenstein, R.P. Hugel Inorg. Chem. 1978 17 1945.
51. H. Bredereck, H.W. Vollmann Chem. Ber. 1972 105 2271.
52. R.D. Rieke, D.E. Stack, B.T. Dawson, T.-C. Wu J. Org. Chem. 1993 58 2483.
53. D.F. DeTar Org. Synth. 1963 Coll. Vol. 4 730.
54. D.F. DeTar, L.A. Carpino J. Am. Chem. Soc. 1956 78 475.
55. J.R. Hwu, C.H. Hsu, F.F. Wong, C. Chung, G.H. Hakemelahi Synthesis 1998 329.