SET photochemistry of phthalimide anion and its reactivity with hydrogen donors

Tetrahedron

Volumn 58, Issue 36, 2002, Pages 7267-7274

  Sánchez Sánchez, Cristobal ^a   Pérez Inestrosa, Ezequiel ^a   García Segura, Rafael ^a   Suau, Rafael ^a  

^a UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

Electron transfer; Imides; Isoindoles; Photochemistry; Radicals and radical reactions

Indexed keywords

1,9B DIHYDRO 9B HYDROXY 5H OXAZOLO[4,3 A]ISOINDOL 5 ONE; 2 METHYL 2 BUTANOL; 2,3 DIHYDRO 3 (HYDROXYMETHYL) 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 (PHENOXYMETHYL) 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 [(1,1 DIMETHYLETHOXY)METHYL] 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 [(4 METHOXYPHENYL)METHYL] 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 [(4 METHYLPHENOXY)METHYL] 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 [[METHYL(PHENYL)AMINO]METHYL] 1H ISOINDOL 1 ONE; 2,3 DIHYDRO 3 HYDROXY 3 [METHOXY(PHENYL)METHYL] 1H ISOINDOL 1 ONE; 3 (2 HYDROXY 2 METHYLPROPYLIDENE) 1H ISOINDOL 1(2H) ONE; 3 (2 METHYL 2 PROPENYLIDENE) 1H ISOINDOL 1(2H) ONE; 4 METHOXYTOLUENE; [1 (DIETHYLAMINO)ETHYL] 2,3 DIHYDRO 3 HYDROXY 1H ISOINDOL 1 ONE; ALCOHOL; ALKADIENE; AMINE; ANION; ANISOLE; BUTANOL; DIHYDRO 3 HYDROXY 1H ISOINDOL 1 ONE; ETHER; HYDROGEN; INDOLE DERIVATIVE; N,N DIMETHYLANILINE; PHTHALIMIDE; TERT BUTYL METHYL ETHER; TOLUENE; TOLUENE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ELECTRON TRANSPORT; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; SYNTHESIS; THERMODYNAMICS;

EID: 0037008940     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00756-1     Document Type: Article

References (43)

1. (a) Kanaoka Y. Acc. Chem. Res. 11:1978;407-413
2. (b) Mazzocchi P.H. Padwa A., Organic Photochemistry. Vol. 5:1981;421-471 Marcel Dekker, New York. Chapter 5
3. (c) Coyle J.D. Horspool W.M., Synthetic Organic Photochemistry. 1984;259-283 Plenum, New York. Chapter 4
4. (d) Mauder H., Griesbeck A.G. Horspool W.M., Song P.-S., CRC Handbook of Organic Photochemistry and Photobiology. 1995;513-521 CRC, Boca Raton, FL. Chapter 42
5. (e) Griesbeck A.G. Chimia. 52:1998;272-283
6. (f) Griesbeck A.G., Kramer W., Oelgemöller M. Synlett. 1999;1169-1178
7. (g) Yoon U.C., Mariano P.S. Acc. Chem. Res. 34:2001;523-533.
8. (a) Kanaoka Y., Sakai K., Murata R., Hatanaka Y. Heterocycles. 3:1975;719-722
9. (b) Frecero M., Fasani E., Albini A. J. Org. Chem. 58:1993;1740-1745.
10. (a) Griesbeck A.G., Oelgemöller M. Synlett. 1999;492-494
11. (b) Griesbeck A.G., Oelgemöller M. Synlett. 2000;71-72
12. (c) Griesbeck A.G., Oelgemöller M., Lex J. Synlett. 2000;1455-1457
13. (d) Griesbeck A.G., Oelgemöller M., Lex J., Haeuseler A., Schmittel M. Eur. J. Org. Chem. 2001;1831-1833.
14. Yoon U.C., Kim J.U., Mariano P.S. Heterocycles. 29:1989;1041-1063.
15. Coyle J.D., Newport G.L., Harriman A. J. Chem. Soc., Perkin Trans. 1978;133-137.
16. (a) Mazzocchi P.H., Minamikawa S., Wilson P. Tetrahedron Lett. 19:1978;4361-4364
17. (b) Maruyama K., Kubo Y. Chem. Lett. 1978;851-854
18. (c) Hayashi H., Nagakura S., Kubo Y., Maruyama K. Chem. Phys. Lett. 72:1980;291-294
19. (d) Mazzocchi P.H., Klingler L. J. Am. Chem. Soc. 106:1984;7567-7572
20. (e) Maruyama K., Kubo Y. J. Org. Chem. 50:1985;1426-1435
21. (f) Mazzocchi P.H., Minamikawa S., Wilson P. J. Org. Chem. 50:1985;2681-2684.
22. (a) Kanaoka Y., Koyama K. Tetrahedron Lett. 13:1972;4517-4520
23. (b) Kanaoka Y., Sato E. Chem. Pharm. Bull. 26:1978;989-992.
24. Lee Y.J., Ling R., Mariano P.S., Yoon U.C., Kim D.U., Oh S.W. J. Org. Chem. 61:1996;3304-3314.
25. Roth H.J., Hundeshagen G. Arch. Pharmaz. 309:1976;58-62.
26. Suau R., García-Segura R., Sánchez-Sanchez C., Pérez-Inestrosa E. Eur. J. Org. Chem. 2002;1903-1911.
27. Suau R., García-Segura R. Tetrahedron Lett. 29:1988;1071-1074.
28. . Oxazolidines are also formed in the addition of hydromethyl radical (photochemically generated from benzophenone/MeOH) to ketoximes: Torrente S., Alonso R. Org. Lett. 3:2001;1985-1987.
29. Sato Y., Nakai H., Wada M., Ogiwara H., Mizoguchi T., Migita Y., Hatanaka Y., Kanaoka Y. Chem. Pharm. Bull. 30:1982;1939-1945.
30. Gramain J.C., Remuson R. J. Org. Chem. 50:1985;1120-1122.
31. Wubbels G.G., Monaco W.J., Johnson D.E., Meredith R.S. J. Am. Chem. Soc. 98:1976;1036-1037.
32. Fossey J., Lefort D., Sorba J. Free Radicals in Organic Chemistry. 1995;Wiley, Chichester. pp 49-72.
33. . Photoinduced electron transfer from phthalimide anion to 1-iodoadamantane has been recently reported: Bajo Maquieira M., Peñéñory A.-B., Rossi R.A. J. Org. Chem. 67:2002;1012-1015.
34. Berci-Filho P., Quina F.H., Gehlen M.H., Politi M.J., Neumann M.G., Barros T.C. J. Photochem. Photobiol. A: Chem. 92:1995;155-161.
35. -4 s. Marquet, J.; Gallardo, I. Universitat Autónoma de Barcelona, Spain, private communication.
36. Rehm D., Weller A. Isr. J. Chem. 8:1970;259-271.
37. Phthalimidyl radical generated by photolysis of N-halophthalimides adds to electron-rich alkenes and alkynes in a chain reaction: (a) Kirsch A., Lüning U. J. Prak. Chem.-Chem. Ztg. 340:1998;129-134 (b) Kirsch A., Lüning U., Krüger O. J. Prak. Chem.-Chem. Ztg. 341:1999;649-656 (c) Wille U., Krüger O., Kirsch A., Lüning U. Eur. J. Org. Chem. 1999;3185-3189.
38. Phthalimidyl radical generated by photolysis of N-halophthalimides adds to electron-rich alkenes and alkynes in a chain reaction: (a) Kirsch A., Lüning U. J. Prak. Chem.-Chem. Ztg. 340:1998;129-134 (b) Kirsch A., Lüning U., Krüger O. J. Prak. Chem.-Chem. Ztg. 341:1999;649-656 (c) Wille U., Krüger O., Kirsch A., Lüning U. Eur. J. Org. Chem. 1999;3185-3189.
39. Phthalimidyl radical generated by photolysis of N-halophthalimides adds to electron-rich alkenes and alkynes in a chain reaction: (a) Kirsch A., Lüning U. J. Prak. Chem.-Chem. Ztg. 340:1998;129-134 (b) Kirsch A., Lüning U., Krüger O. J. Prak. Chem.-Chem. Ztg. 341:1999;649-656 (c) Wille U., Krüger O., Kirsch A., Lüning U. Eur. J. Org. Chem. 1999;3185-3189.
40. The photoaddition of THF to NMP has been reported. (a) Kanaoka Y., Hatanaka Y. Chem. Pharm. Bull. 22:1974;2205-2206 (b) Roth H.J., Schwarz D. Arch. Pharmaz. 309:1975;52-58.
41. The photoaddition of THF to NMP has been reported. (a) Kanaoka Y., Hatanaka Y. Chem. Pharm. Bull. 22:1974;2205-2206 (b) Roth H.J., Schwarz D. Arch. Pharmaz. 309:1975;52-58.
42. Horii Z.I., Tamura Y. J. Org. Chem. 26:1961;2273-2276.
43. Marsini A., Scartoni V. Gazz. Chim. Ital. 102:1972;507-516.