Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 263-269

  Itou, Tatsuya ^a   Yoshimi, Yasuharu ^a   Morita, Toshio ^a   Tokunaga, Yuji ^a   Hatanaka, Minoru ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

10 METHOXYDECANE; 2 (10 METHOXYDECYL) 1 CYANOBENZENE; 2 BENZYL 1 CYANOBENZENE; 2 CYCLOHEXYL 1 CYANOBENZENE; 2 PENTYL 1 CYANOBENZENE; 2 TERT BUTYL 1 CYANOBENZENE; 3 (10 METHOXYDECYL) 1 CYANOBENZENE; 3 CYCLOHEXYL 1 CYANOBENZENE; 3 PENTYL 1 CYANOBENZENE; 3 TERT BUTYL 1 CYANOBENZENE; 4 (10 METHOXYDECYL) 1 CYANOBENZENE; 4 (10 METHOXYDECYL) 1,2 DICYANOBENZENE; 4 (10 METHOXYDECYL) 1,3 DICYANOBENZENE; 4 (2 BUTYLHEPTYL) 1 CYANOBENZENE; 4 BENZYL 1 CYANOBENZENE; 4 BENZYL 1,2 DICYANOBENZENE; 4 CYCLOBENZENE 1,3 DICYANOBENZENE; 4 CYCLOHEXYL 1 CYANOBENZENE; 4 CYCLOHEXYL 1,2 DICYANOBENZENE; 4 METHYL 1 CYANOBENZENE; 4 PENTYL 1 CYANOBENZENE; 4 PENTYL 1,2 DICYANOBENZENE; 4 PENTYL 1,3 DICYANOBENZENE; 4 TERT BUTYL 1 CYANOBENZENE; 9 CYANOPHENANTHRENE; 9,10 DIHYDRO 9 CYANOPHENANTHRENE; BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DICYANOBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DECARBOXYLATION; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; PHOTOREACTIVITY; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 56949087916     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.054     Document Type: Article

References (50)

1. Abdoh M.M.M., Shivaprakash S.N.C., and Shashidhara Prasad J. J. Chem. Phys. 77 (1982) 2570-2576
2. Ichimura H., Shirakawa T., Tokuda T., and Seimiya T. Bull. Chem. Soc. Jpn. 56 (1983) 2238-2240
3. Osman M.A., Schad Hp., and Zeller H.R. J. Chem. Phys. 78 (1983) 906-914
4. Schad Hp., and Osman M.A. J. Chem. Phys. 79 (1983) 5710-5717
5. Larock R.C. Comprehensive Organic Transformations (1989), VCH, New York, NY 819
6. Grundmann C. In: Falbe J. (Ed). Houben-Weyl: Methoden der organischen Chemie. 4th ed. Vol. E5 (1985), Georg Thieme, Stuttgart 1313
7. Zienkiewicz J., Fryszkowska A., Zienkiewicz K., Guo F., Kaszynski P., Januszko A., and Jones D. J. Org. Chem. 72 (2007) 3510-3520
8. Takagi K., Okamoto T., Sakakibara Y., and Oka S. Chem. Lett. (1973) 471-474
9. Anderson B.A., Bell E.C., Ginah F.O., Harn N.K., Pagh L.M., and Wepsiec J.P. J. Org. Chem. 63 (1998) 8224-8228
10. Schareina T., Zapf A., and Beller M. Chem. Commun. (2004) 1388-1389
11. Schareina T., Zapf A., Mägerlein W., Müller N., and Beller M. Tetrahedron Lett. 48 (2007) 1087-1090
12. Ellis G.P., and Romney-Alexander T.M. Chem. Rev. 87 (1987) 779-794
13. Zanon J., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 2890-2891
14. Schareina T., Zapf A., and Beller M. Tetrahedron Lett. 46 (2005) 2585-2588
15. Tan C., Zheng X., Ma Z., and Gu Y. Synth. Commun. 29 (1999) 123-127
16. Borg R.M., Arnold D.R., and Cameron T.S. Can. J. Chem. 62 (1984) 1785-1802
17. Arnold D.R., and Du X. J. Am. Chem. Soc. 111 (1989) 7666-7667
18. Torriani R., Mella M., Fasani E., and Albini A. Tetrahedron 53 (1997) 2573-2580
19. Mangion D., and Arnold D.R. Acc. Chem. Res. 35 (2002) 297-304
20. Mizuno K., Ikeda M., and Otsuji Y. Tetrahedron Lett. 26 (1985) 461-466
21. Mizuno K., Nakanishi K., and Otsuji Y. Chem. Lett. (1988) 1833-1836
22. Nakanishi K., Mizuno K., and Otsuji Y. Bull. Chem. Soc. Jpn. 66 (1993) 2371-2379
23. Kyushin S., Masuda Y., Matsushita K., Nakadaira Y., and Ohashi M. Tetrahedron Lett. 31 (1990) 6395-6398
24. Kako M., and Nakadaira Y. Bull. Chem. Soc. Jpn. 73 (2000) 2403-2422
25. Ohashi M., and Miyake K. Chem. Lett. (1977) 615-616
26. Ohashi M., Miyake K., and Tsujimoto K. Bull. Chem. Soc. Jpn. 53 (1980) 1683-1688
27. Pac C., Nakasone A., and Sakurai H. J. Am. Chem. Soc. 99 (1977) 5806-5808
28. Majima T., Pac C., Nakasone A., and Sakurai H. J. Chem. Soc., Chem. Commun. (1978) 490-491
29. Majima T., Pac C., and Sakurai H. J. Am. Chem. Soc. 102 (1980) 5265-5273
30. Majima T., Pac C., Nakasone A., and Sakurai H. J. Am. Chem. Soc. 103 (1981) 4499-4508
31. Yoshimi Y., Itou T., and Hatanaka M. Chem. Commun. (2007) 5244-5246
32. Tsujimoto K., Nakao N., and Ohashi K. J. Chem. Soc. Chem. Commun. (1992) 366-367
33. When dry acetonitrile was used as a solvent, the carboxylate ions did not dissolve in the solution.
34. Schuster G.B., and Lan J.Y. J. Am. Chem. Soc. 107 (1985) 6710-6711
35. {radical dot}-); reduction potential of 1, Es; excited singlet energy of 1
36. Kavarnos G.J., and Turro N.J. Chem. Rev. 86 (1986) 401-449
37. Murov S.L., Carmichalez I., and Hug G.L. Handbook of Photochemistry (1993), Marcel Dekker, New York, NY p 271
38. Galicia M., and Gonzalez F.J. J. Electrochem. Soc. 149 (2002) D46-D50
39. -) slightly depend on R. Thus, for other carboxylate ions 2b-e, negative values of ΔG would be obtained:. Billing R., Zakharova G.V., Atabekyan L.S., and Hennig H. J. Photochem. Photobiol., A 59 (1991) 163-174
40. The decarboxylation of carboxylate ions having an electron-withdrawing group such as lithium acetoacetate, potassium monoethyl malonate, and sodium cyanoacetate proceeded efficiently both in the absence and in the presence of Phen; however, the substituted product 3 was not obtained, since the generated radicals were readily reduced via the BET to yield the corresponding anions.
41. Yokoi H., Nakano T., Fujita W., Ishiguro K., and Sawaki Y. J. Am. Chem. Soc. 120 (1998) 12453-12458
42. Wang C., Russell G.A., and Trahanovsky W.S. J. Org. Chem. 63 (1998) 9956
43. Mizuno K., Pac C., and Sakurai H. J. Chem. Soc., Chem. Commun. (1975) 553
44. Yasuda M., Pac C., and Sakurai H. J. Chem. Soc., Perkin Trans. 1 (1981) 746-750
45. Grossman O., and Gelman D. Org. Lett. 8 (2006) 1189-1190
46. Seomoon D., and Phil H.L. J. Org. Chem. 73 (2008) 1165-1168
47. Flaherty A., Trunkfield A., and Barton W. Org. Lett. 7 (2005) 4975-4978
48. Yoshimi Y., Ishise A., Oda H., Moriguchi Y., Kanezaki H., Nakaya Y., Katsuno K., Itou T., Inagaki S., Morita T., and Hatanaka M. Tetrahedron Lett. 49 (2008) 3400-3404
49. Quintana I., Boersma A.J., Pena D., and Guitian E. Org. Lett. 8 (2006) 3347-3349
50. Kim Y.H., Lee H., Kim Y.J., Kim B.T., and Heo J.-N. J. Org. Chem. 73 (2008) 495-501