The role of SET in the deprotection of (thio)ketals under photosensitization by π-acceptors

Tetrahedron

Volumn 53, Issue 6, 1997, Pages 2219-2232

  Fasani, Elisa ^a   Freccero, Mauro ^a   Mella, Mariella ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; ACETAL; KETONE;

ACETYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; ELECTRON TRANSPORT; PHOTOOXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031562103     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01123-4     Document Type: Article

References (60)

1. 1. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis; Wiley: New York, 1991
2. 2. Pillai, V.R.N., Org. Photochem. 1987, 9, 225. Pillai, V.R.N., Synthesis 1980, 1
3. 2. Pillai, V.R.N., Org. Photochem. 1987, 9, 225. Pillai, V.R.N., Synthesis 1980, 1
4. 3. Hebert, J.; Gravel, D. Can. J. Chem. 1974, 52, 187. Gravel, D.; Hebert, J.; Thoraval, D. Can. J. Chem. 1983, 61, 400
5. 3. Hebert, J.; Gravel, D. Can. J. Chem. 1974, 52, 187. Gravel, D.; Hebert, J.; Thoraval, D. Can. J. Chem. 1983, 61, 400
6. 4. Takahashi, T.; Nakamura, C.Y.; Satoh, J.Y. J. Chem. Soc., Chem. Commun. 1977, 680
7. 5. Oikawa, Y.; Tanaka, T.; Horita, K. Tetrahedron Lett. 1984, 25, 5393. Schmittel, M.; Levis, M. Synlett. 1996, 315
8. 5. Oikawa, Y.; Tanaka, T.; Horita, K. Tetrahedron Lett. 1984, 25, 5393. Schmittel, M.; Levis, M. Synlett. 1996, 315
9. 6. Tanemura, K.; Suzuki, T. Horaguchi, T. J. Chem. Soc., Chem. Commun. 1992, 979
10. 7. Oku, A.; Kinugasa, M.; Kamada, T. Chem. Lett. 1993, 165. Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2394
11. 7. Oku, A.; Kinugasa, M.; Kamada, T. Chem. Lett. 1993, 165. Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2394
12. 8. Tanemura, K.; Suzuchi, T.; Horaguchi, T. Bull. Chem. Soc. Jpn. 1994, 67, 290. Tanemura, K.; Dohya, H.; Imamura, M.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 453
13. 8. Tanemura, K.; Suzuchi, T.; Horaguchi, T. Bull. Chem. Soc. Jpn. 1994, 67, 290. Tanemura, K.; Dohya, H.; Imamura, M.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 453
14. 9. Masui, M.; Kawaguchi, T.; Ozaki, S. J. Chem. Soc., Chem. Commun. 1985, 1484. Noyori, R.; Kurimoto, I. J. Chem. Soc., Chem. Commun. 1986, 1425
15. 9. Masui, M.; Kawaguchi, T.; Ozaki, S. J. Chem. Soc., Chem. Commun. 1985, 1484. Noyori, R.; Kurimoto, I. J. Chem. Soc., Chem. Commun. 1986, 1425
16. 10. Gourcy, J.; Martingly, P.; Simonet, J.; Jeminet, G. Tetrahedron 1981, 37, 1495. Platen, M.; Steckhan, E. Chem. Ber. 1984, 117, 1679
17. 10. Gourcy, J.; Martingly, P.; Simonet, J.; Jeminet, G. Tetrahedron 1981, 37, 1495. Platen, M.; Steckhan, E. Chem. Ber. 1984, 117, 1679
18. 11. Kamata, M.; Kato, Y.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 4349. Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett. 1992, 33, 5085. Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821
19. 11. Kamata, M.; Kato, Y.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 4349. Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett. 1992, 33, 5085. Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821
20. 11. Kamata, M.; Kato, Y.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 4349. Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett. 1992, 33, 5085. Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821
21. 12. Garcia, H.; Iborra, S.; Miranda, M.. A.; Primo, J. New J. Chem. 1989, 13, 805. Yan, B.Z.; Zhang, Z.G.; Yuan, H.C.; Wang, L.C.; Xu, J.H. J. Chem. Soc., Perkin Trans. 2 1994, 2545
22. 12. Garcia, H.; Iborra, S.; Miranda, M.. A.; Primo, J. New J. Chem. 1989, 13, 805. Yan, B.Z.; Zhang, Z.G.; Yuan, H.C.; Wang, L.C.; Xu, J.H. J. Chem. Soc., Perkin Trans. 2 1994, 2545
23. 13. Fox, M.A.; Chanon, M. Photoinduced Electron Transfer, Elsevier, Amstderdam: 1988
24. 14. Mattes, S.L.; Farid, S. Org. Photochem. 1983, 6, 233
25. 15. Albini, A.; Mella, M.; Freccero, M. Tetrahedron 1994, 50, 575. Saeva, F.D. Top. Curr. Chem. 1991, 156, 59
26. 15. Albini, A.; Mella, M.; Freccero, M. Tetrahedron 1994, 50, 575. Saeva, F.D. Top. Curr. Chem. 1991, 156, 59
27. 16. Mella, M.; Fasani, E.; Albini, A. J. Org. Chem. 1992, 57, 3051
28. 17. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259
29. 18. Steichen, D.S.; Foote, C.S. J. Am. Chem. Soc. 1981, 103, 1855. Araki, Y.; Dobrowolski, D.C.; Goyne, T.E.; Hanson, D.C.; Jiang, Z.Q.; Lee, K.J.; Foote, C.S. J. Am. Chem. Soc. 1984, 106, 4570. Tsuchya, M.; Ebbesen, T.W.; Nishimura, Y.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1987, 2121. Albini, A.; Spreti, S. Gazz. Chim. Ital. 1985, 115, 227
30. 18. Steichen, D.S.; Foote, C.S. J. Am. Chem. Soc. 1981, 103, 1855. Araki, Y.; Dobrowolski, D.C.; Goyne, T.E.; Hanson, D.C.; Jiang, Z.Q.; Lee, K.J.; Foote, C.S. J. Am. Chem. Soc. 1984, 106, 4570. Tsuchya, M.; Ebbesen, T.W.; Nishimura, Y.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1987, 2121. Albini, A.; Spreti, S. Gazz. Chim. Ital. 1985, 115, 227
31. 18. Steichen, D.S.; Foote, C.S. J. Am. Chem. Soc. 1981, 103, 1855. Araki, Y.; Dobrowolski, D.C.; Goyne, T.E.; Hanson, D.C.; Jiang, Z.Q.; Lee, K.J.; Foote, C.S. J. Am. Chem. Soc. 1984, 106, 4570. Tsuchya, M.; Ebbesen, T.W.; Nishimura, Y.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1987, 2121. Albini, A.; Spreti, S. Gazz. Chim. Ital. 1985, 115, 227
32. 18. Steichen, D.S.; Foote, C.S. J. Am. Chem. Soc. 1981, 103, 1855. Araki, Y.; Dobrowolski, D.C.; Goyne, T.E.; Hanson, D.C.; Jiang, Z.Q.; Lee, K.J.; Foote, C.S. J. Am. Chem. Soc. 1984, 106, 4570. Tsuchya, M.; Ebbesen, T.W.; Nishimura, Y.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1987, 2121. Albini, A.; Spreti, S. Gazz. Chim. Ital. 1985, 115, 227
33. 19a. Chin, D.H.; Chiericato, G.; Nanni, E.J.; Sawyer, D.T. J. Am. Chem. Soc. 1982, 104, 1296
34. b. Sawyer, D.T.; Valentine, J.S. Acc. Chem. Res. 1981, 14, 393.
35. c. Schaap, A.P.; Lopez, L.; Gagnon, S.D. J. Am. Chem. Soc. 1983, 105, 663..
36. d. Akaba, R.; Sakuragi, H.; Tokumaru, K. J. Chem. Soc., Perkin Trans 2, 1991, 291.
37. e. Lopez, L. Top. Curr. Chem. 1990, 156, 117.
38. f. Fukuzumi, K.; Tanii, K.; Ishikawa, M.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1989, 1801
39. 20a. Direct measurements of the basicity are not available. A pKa value of-1.9 in water has been estimated, ref. 20b, and the value in an aprotic solvent is certainly largely positive.
40. b. Baciocchi, E.; Del Giacco, T.; Elisei, F.; Ioele, M. J. Org. Chem. 1995, 60, 7974.
41. c. Wagner, P.J.; Truman, R.J.; Puchalski, A.E.; Wake, R. J. Am. Chem. Soc. 1986, 108, 7727
42. 21. Bonifacic, M.; Asmus, K.D. J. Org. Chem. 1986, 51, 1216
43. 22. For an analogy see: Hashimoto, S.; Kurimoto, I.; Fujii, Y.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 1427. Noyori, R.; Kurimoto, I. J. Chem. Soc., Chem. Commun. 1986, 1425
44. 22. For an analogy see: Hashimoto, S.; Kurimoto, I.; Fujii, Y.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 1427. Noyori, R.; Kurimoto, I. J. Chem. Soc., Chem. Commun. 1986, 1425
45. 23a. Wayner, D.D.M.; Dannenberg, J.J.; Griller, D. Chem. Phys. Lett. 1986, 131, 189.
46. -1 since it is reported that in aprotic solvents, this is close to the S-H BDE, ref. 23c,d; the Eox of the 2-dithiolanyl radical is estimated as -0.8 V by modification of that of the 2-dioxolanyl radical, see above.
47. c. Inbar, S.; Linschitz, H.; Cohen, S.G. J. Am. Chem. Soc. 1982, 104, 1679.
48. d. Fine, D.H.; Westmore, J.B. Can. J. Chem. 1970, 48, 395
49. 24. Gleiter, R.; Hoffmann, H.; Irngartinger, H.; Nixdorf, M. Chem. Ber. 1994, 127, 2215
50. 25. Sweigart, D.A.; Turner, D.W. J. Am. Chem. Soc. 1972, 94, 5599
51. 26. Miller, L. J. Org. Chem. 1972, 37, 916
52. 27. Kavarnos, G.J.; Turro, N.J. Chem. Rev. 1986, 86, 401
53. 28. Fukuzumi, S.; Kuroda, S.; Taroka, T. J. Chem. Soc., Chem. Commun. 1986, 1553. Poulos, A.T.; Hammond, G.S.; Burton, M.E. Photochem. Photobiol. 1981, 34, 169. Gebert, H.; Regenstein, W.; Bendig, J.; Kreysig, D. Z. Phys. Chem. (Leipzig) 1982, 263, 65. Bendig J.; Kreysig, D.; Gebert, H.; Regenstein, W. J. prakt. Chem. 1979, 321, 420
54. 28. Fukuzumi, S.; Kuroda, S.; Taroka, T. J. Chem. Soc., Chem. Commun. 1986, 1553. Poulos, A.T.; Hammond, G.S.; Burton, M.E. Photochem. Photobiol. 1981, 34, 169. Gebert, H.; Regenstein, W.; Bendig, J.; Kreysig, D. Z. Phys. Chem. (Leipzig) 1982, 263, 65. Bendig J.; Kreysig, D.; Gebert, H.; Regenstein, W. J. prakt. Chem. 1979, 321, 420
55. 28. Fukuzumi, S.; Kuroda, S.; Taroka, T. J. Chem. Soc., Chem. Commun. 1986, 1553. Poulos, A.T.; Hammond, G.S.; Burton, M.E. Photochem. Photobiol. 1981, 34, 169. Gebert, H.; Regenstein, W.; Bendig, J.; Kreysig, D. Z. Phys. Chem. (Leipzig) 1982, 263, 65. Bendig J.; Kreysig, D.; Gebert, H.; Regenstein, W. J. prakt. Chem. 1979, 321, 420
56. 28. Fukuzumi, S.; Kuroda, S.; Taroka, T. J. Chem. Soc., Chem. Commun. 1986, 1553. Poulos, A.T.; Hammond, G.S.; Burton, M.E. Photochem. Photobiol. 1981, 34, 169. Gebert, H.; Regenstein, W.; Bendig, J.; Kreysig, D. Z. Phys. Chem. (Leipzig) 1982, 263, 65. Bendig J.; Kreysig, D.; Gebert, H.; Regenstein, W. J. prakt. Chem. 1979, 321, 420
57. 29. Mella, M.; d'Alessandro, N.; Freccero, M.; Albini, A. J. Chem. Soc., Perkin Trans. 2 1993, 515
58. 30. Wintgens, V.; Kossanyi, J.; Sinalty, M. Bull. Chem. Soc. Fr. 1983, 11, 115
59. 31. Photoinduced SET from thioethers to aromatic nitriles has been previously documented. Beecroft, R.A.; Davidson, R.S.; Goodwin, B.; Pratt, J.E. Tetrahedron 1984, 40, 4487
60. 32. Mella, M.; Freccero, M.; Albini, A. Tetrahedron 1996, 52, 5549