2,4,6-Trisubstituted Pyridines. Synthesis, Fluorescence, and Scintillator Properties

Journal of the American Chemical Society

Volumn 95, Issue 15, 1973, Pages 4891-4895

  Maria Del Carmen, G Barrio ^a,b   Barrio, Jorge R ^a,b   Walker, Graham ^a,b   Novelli, Armando ^a,b   Leonard, Nelson J ^a,b  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344356125     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00796a021     Document Type: Article

References (47)

1. M. L. Moore, Org. React., 5, 301 (1949).
2. F. Chubb, A. S. Hay, and R. B. Sandin, J. Amer. Chem. Soc., 75, 6042 (1953).
3. W. Dilthey, J. Prakt. Chem., 102, 209 (1921).
4. R. Lombard and J. P. Stephan, Bull. Soc. Chim. Fr., 1458 (1958).
5. W. Zecher and F. Kröhnke, Chem. Ber., 94, 690 (1961).
6. R. L. Frank and R. P. Seven, J. Amer. Chem. Soc., 71, 2629 (1949), and references therein.
7. H. Bredereck, R. Gompper, H. G. v. Schuh, and G. Theilig, Angew. Chem., 71, 753 (1959).
8. H. Bredereck, R. Gompper, H. G. v. Schuh, and G. Theilig, Newer Methods Prep. Org. Chem., 3, 241 (1964).
9. H. W. Gibson, Chem. Rev., 69, 673 (1969).
10. P. A. S. Smith and A. J. Macdonald, J. Amer. Chem. Soc., 72, 1037 (1950).
11. W. H. Davies and M. A. T. Rogers, J. Chem. Soc., 126 (1944).
12. M. Mousseron, R. Jacquier, and R. Zagdoun, Bull. Soc. Chim. Fr., 197 (1952).
13. V. Komarov, E. A. Chernikova, and G. V. Komarov, Zh. Fiz. Khim., 36, 540 (1962);
14. Chem. Abstr., 57, 1605 (1962).
15. A. N. Kost and I. I. Grandberg, Zh. Obshch. Khim., 25, 1432 (1955);
16. Chem. Abstr., 50, 4800 (1956).
17. D. S. Noyce and F. W. Bachelor, J. Amer. Chem. Soc., 74, 4577 (1952).
18. A. Chatterjee and R. Raychaudhuri, J. Org. Chem., 33, 2546 (1968).
19. D. Elad, Proc. Chem. Soc., London, 225 (1962).
20. D. Elad, Chem. Ind. (London), 362 (1962).
21. D. Elad and J. Rokach, J. Org. Chem., 29, 1855 (1964).
22. D. Elad and J. Rokach, J. Org. Chem., 30, 3361 (1965).
23. D. Elad and J. Rokach, J. Chem. Soc., 800 (1965).
24. D. Elad, Angew. Chem. Int. Ed. Engl., 5, 255 (1966).
25. M. Fish and G. Ourisson, Bull. Soc. Chim. Fr., 1325 (1966).
26. A. Rieche, E. Schmitz, and E. Gruendemann, Z. Chem., 4, 177 (1964).
27. A. Rieche, E. Schmitz, and E. Gruendemann, Angew. Chem., 73, 621 (1961).
28. M. Weiss [J. Amer, Chem. Soc., 74, 200 (1952)] isolated 2,4,6-triphenylpyridine and benzylacetophenone (low yield) from the reaction between benzaldehyde and acetophenone in ammonium acetate and glacial acetic acid.
29. Dihydropyridines are known to disproportionate to form pyridine and piperidine derivatives; see M. Scholtz, Ber., 30, 2295 (1897);
30. K. W. Merz and H. Richter, Arch. Pharm.y 275, 294 (1937).
31. D. H. Hey, C. J. M. Stirling, and G. H. Williams, J. Chem. Soc 3963 (1955).
32. J. Overhoff and J. P. Wibaut, Reel. Trav. Chim. Pays-Bas, 50, 957 (1931).
33. A. E. Gillam, D. H. Hey, and A. Lambert, J. Chem. Soc., 364 (1941).
34. P. Krumholz, J. Amer. Chem. Soc., 73, 3487 (1951).
35. A. P. Phillips and P. L. Graham, J. Amer. Chem. Soc., 74, 1552 (1952).
36. L. Sobczyk, Bull. Acad. Pol. Sei., 9, 237 (1961).
37. Studies on the dissociation constants of phenylpyridines32 showed 2-phenylpyridine to be a very weak base. Earlier work [W. Dilthey, H. Nusslein, H. Meyer, and H. Kaffer, J. Prakt. Chem., 104, 28 (1922)] demonstrated that 2,4,6-triphenylpyridine was also a very weak base.
38. Upon excitation they can be expected to become more basic: A. Weller, Progr. React. Kinet., 1, 189 (1961).
39. T. Förster, Z. Elektrochem., 54, 531 (1950).
40. D. M. Hercules and L. B. Rogers, Spectrochim. Acta, 14, 393 (1959).
41. It has been shown, for example, that the transition in the p-haloanisoles requires electron acceptance by the halogen: W. M. Schubert, J. M. Craven, and H. Steadly, J. Amer. Chem. Soc., 81, 2695 (1959).
42. H. H. Jaffé and M. Orchin, “Theory and Application of Ultraviolet Spectroscopy,” Wiley, New York, N. Y., 1966.
43. S. J. Strickler and R. Berg, J. Chem. Phys., 37, 814 (1962).
44. M. P. Neary and A. L. Budd, “The Current Status of Liquid Scintillation Counting,” E. D. Bransome, Ed., Gruñe and Stratton, New York, N. Y., 1970, p 273.
45. F. Snyder, ref 41, p 248.
46. R. D. Spencer and G. Weber, Ann. N. Y. Acad. Sei., 158, 361 (1969).
47. T. G. Scott, R. D. Spencer, N. J. Leonard, and G. Weber, J. Amer. Chem. Soc., 92, 687 (1970).