New modes of reactivity in the threshold of the reduction potential in solution. alkylation of lithium PAH (Polycyclic Aromatic Hydrocarbon) dianions by primary fluoroalkanes: A reaction pathway complementing the classical birch reductive alkylation

Chemistry - A European Journal

Volumn 13, Issue 36, 2007, Pages 10096-10107

  Melero, Cristóbal ^a   Herrera, Raquel P ^a   Guijarro, Albert ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Alkylation; Fluoroalkanes; Lithium; Polyaromatic hydrocarbons (PAHs); Semiempirical calculations

Indexed keywords

ALKYLATION; CHEMICAL REACTIVITY; FLUORINE COMPOUNDS; LITHIUM COMPOUNDS; NUCLEOPHILES;

FLUOROALKANES; REGIOISOMERS; SEMIEMPIRICAL CALCULATIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 38049098721     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700187     Document Type: Article

References (74)

1. R. P. Herrera, A. Guijarro, M. Yus, Tetrahedron Lett. 2003, 44, 1309-1312.
2. M. Yus; R. P. Herrera, A. Guijarro, Chem. Eur. J. 2002, 8, 2574-2584.
3. R. P. Herrera, A. Guijarro, M. Yus, Tetrahedron Lett. 2003, 44, 1313-1316.
4. C. Melero, A. Guijarro, M. Yus, Tetrahedron Lett. 2006, 47, 6267-6271.
5. M. Yus in The Chemistry of Organolithium Compounds, Part 2, Vol. 1 (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2004, pp. 657-747.
6. a) A. Guijarro, R. D. Rieke, Angew. Chem. 1998, 110, 1789-1791:
7. Angew. Chem. Int. Ed. 1998, 37, 1679-1681;
8. b) A. Guijarro, D. M. Rosenberg, R. D. Rieke, J. Am. Chem. Soc. 1999, 121, 4155-4167.
9. R. D. Chambers, S. R. James in Comprehensive Organic Chemistry, Vol 1 (Eds.: D. Barton, W. D. Ollis), Pergamon Press, New York, 1979, p. 527.
10. K. Meerholz, J. Heinze, J. Am. Chem. Soc. 1989, 111, 2325-2326.
11. R. P. Herrera, A. Guijarro, M. Yus, Tetrahedron Lett. 2001, 42, 3455-3458.
12. G. Levin, B. E. Holloway, M. Szwarc, J. Am. Chem. Soc. 1976, 98, 5706-5709.
13. J. J. Brooks, W. Rhine, G. D. Stucky, J. Am. Chem. Soc. 1972, 94, 7346-7351.
14. R. Benken, H. Günther, Helv. Chim. Acta 1988, 71, 694-702.
15. J. F. Garst, Acc. Chem. Res. 1971, 4, 400-406.
16. a) J. F. Garst, F. E. Barton II, Tetrahedron Lett. 1969, 10, 587-590;
17. b) J. F. Garst, F. E. Barton II, J. Am. Chem. Soc. 1974, 96, 523-529.
18. W. Huber, A. May, K. Müllen, Chem. Ber. 1981, 114, 1318-1336.
19. a) A. N. Sidorov, Opt. Spektrosk. 1979, 47, 678-683
20. (Chem. Abstr. 1979, 92:110107;
21. b) J. P. Devlin, J. S. McKennis, C. Thornton, J. C. Moore, J. Phys. Chem. 1982, 86, 2613-2616.
22. J. J. Eisch, J. Org. Chem. 1963, 28, 707-710.
23. R. G. Pearson, R. L. Dillon, J. Am. Chem. Soc. 1953, 75, 2439-2443.
24. a) P. Hohenberg, W. Kohn, Phys. Rev. B 1964, 136, 864-871;
25. b) W. Kohn, L. Sham, J. Phys. Rev. A 1965, 140, 1133-1138.
26. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
27. b) P. J. Stephens, F. J. Devlin, C. F. Chablowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
28. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654.
29. D. F. Lindow, C. N. Cortez, R. G. Harvey, J. Am. Chem. Soc. 1972, 94, 5406-5412.
30. K. Müllen, Helv. Chim. Acta 1978, 61, 1296-1304.
31. a) A. Minsky, A. Y. Meyer, M. Rabinovitz, Angew. Chem. 1983, 95, 45-46;
32. Angew. Chem. Int. Ed. Engl. 1983, 22, 45-46;
33. b) A. Minsky, A. Y. Meyer, M. Rabinovitz, Tetrahedron Lett. 1982, 23, 5351-5354.
34. R. Frim, A. Mannschreck, M. Rabinovitz, Angew. Chem. 1990, 102, 919-920;
35. Angew. Chem. Int. Ed. Engl. 1990, 29, 919-921.
36. A. Ioffe, A. Ayalon, M. Rabinovitz, J. Chem. Soc. Perkin Trans. 2 1994, 1115-1116.
37. a) P. W. Rabideau, R. G. Harvey, J. Org. Chem. 1970, 35, 25-30;
38. b) P. W. Rabideau, R. G. Harvey, J. B. Stothers, Chem. Commun. 1969, 1005-1006.
39. R. G. Harvey, C. C. Davis, J. Org. Chem. 1969, 34, 3007-3009.
40. R. G. Lawer, C. V. Ristagno, J. Am. Chem. Soc. 1969, 91, 1534-1535.
41. R. H. Cox, H. W. Terry, Jr., L. W. Harrison, Tetrahedron Lett. 1971, 12, 4815-4818.
42. J. L. Mooney, Z. Marcinow, P. W. Rabideau, J. Org. Chem. 1986, 51, 527-532.
43. N. Ahmad, C. Cloke, I. K. Hatton, N. J. Lewis, J. MacMillan, J. Chem. Soc. Perkin Trans. 1 1985, 1849-1858.
44. B. C. Becker, W. Huber, C. Schnieders, K. Müllen, Chem. Ber. 1983, 116, 1573-1594.
45. K. Müllen, W. Huber, G. Neumann, C. Schnieders, H. Unterberg, J. Am. Chem. Soc. 1985, 107, 801-807.
46. O. W. Howarth, G. K. Fränkel, J. Chem. Phys. 1970, 52, 6258-6267.
47. K. Müllen. Helv. Chim. Acta 1978, 61, 2307-2317.
48. C. Tintel, J. Cornelisse, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1983, 102, 231-235.
49. C. Tintel, J. Cornelisse, J. Lugtenburg. Recl. Trav. Chim. Pays-Bas 1983, 102, 14-20.
50. R. G. Harvey, P. W. Rabideau, Tetrahedron Lett. 1970, 11, 3695-3698.
51. M. A. Hempenius, P. P. J. Mulder, C. Erkelens, H. Zuilhof, W. Heinen, J. Lugtenburg, J. Cornelisse, J. Org. Chem. 1993, 58, 3076-3084.
52. a) C. Schnieders, K. Müllen, W. Huber, Tetrahedron 1984, 40, 1701-1711;
53. b) C. Tintel, J. Lugtenburg, G. A. J. Van Amsterdam, C. Erkelens, J. Cornelisse, Recueil: Recl. Trav. Chim. Pays-Bas 1983, 102, 228-231.
54. T. Saji, S. Aoyagui, Electroanal. Chem. 1983, 144, 143-152.
55. A. Minsky, A. Y. Meyer, M. Rabinovitz, Tetrahedron Lett. 1982, 23, 5351-5354.
56. R. E. Hoffman, N. Treitel, E. Shabtai, R. Benshafrut, M. Rabinovitz, Perkin 2 2000, 1007-1011.
57. R. G. Harvey, J. Org. Chem. 1971, 36, 3306-3311.
58. A. Minsky, A. Y. Meyer, R. Poupko, M. Rabinovitz, J. Am. Chem. Soc. 1983, 105, 2164-2172.
59. R. G. Harvey, K. Urberg, J. Org. Chem. 1968, 33, 2206-2211.
60. H. M. Lee, R. G. Harvey, J. Org. Chem. 1979, 44, 4948-4953.
61. K. Meerholz, J. Heinze, Electrochim. Acta 1996, 41, 1839-1854.
62. a) A. Bohnen, W. Heitz, K. Müllen, H. J. Räder, R. Schenk, Makromol. Chem. 1991, 192, 1679-1993;
63. b) C. G. Screttas, M. Micha-Screttas, J. Org. Chem. 1963, 48, 153-158.
64. R. G. Harvey, D. F. Lindow, P. W. Rabideau, J. Am. Chem. Soc. 1972, 94, 5412-5420.
65. N. J. Flint, B. J. Tabner, J. Chem. Soc. Perkin Trans. 2 1986, 1815-1820.
66. B. Eliasson, U. Edlund, J. Chem. Soc. Perkin Trans. 2 1983, 1837-1842.
67. L. D. Kershner, J. M. Gaidis, H. H. Freedman, J. Am. Chem. Soc. 1972, 94, 985-986.
68. W. E. Rhine, J. H. Davis, G. Stucky, J. Organomet. Chem. 1977, 134, 139-149.
69. I. L. Fedushkin, G. V. Khoroshen'kov, M. N. Bochkarev, S. Mühle, H. Schumann, Russ. Chem. Bull. 2003, 52, 1358-1362.
70. M. E. Van Loo, J. Lugtenburg, J. Cornelisse. Eur. J. Org. Chem. 2000, 713-721.
71. S. P. Solodovnikov, S. T. Ioffe, Y. B. Zaks, M. I. Kabachnik, Izv. Akad. Nauk SSSR Ser. Khim. 1968, 442-444
72. (Chem. Abstr. 1968, 69:76168.
73. http://monographs.iarc.fr/ENG/Classification/index.php
74. J. F. Collins, J. P. Brown, G. V. Alexeeff, A. G. Salmon. Regul. Toxicol. Pharmacol. 1998, 28, 45-54.