An efficient photo-SET-induced cleavage of dithiane-carbonyl adducts and its relevance to the development of photoremovable protecting groups for ketones and aldehydes

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9924-9931

  McHale, William A ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5ALPHA CHOLESTAN 3 ONE; ACETOPHENONE; ALDEHYDE; BENZALDEHYDE; BENZOPHENONE; CARBONYL DERIVATIVE; CARBONYLDITHIANE DERIVATIVE; CYCLOHEXANONE; HEPTYL ALDEHYDE; KETONE; PROPIONALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON TRANSPORT; MATHEMATICAL COMPUTING; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; PHOTOSENSITIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; THEORY;

EID: 0032567489     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981697y     Document Type: Article

References (78)

1. (a) For a review on 2-nitrobenzyl, see: Morrison, H. A. Chemistry of the Nitro and Nilroso Groups; John Wiley: New York, 1970; pp 185-191.
2. (b) Misetic, A.; Boyd, M. K. Tetrahedron. Lett. 1998, 39, 1653-1656.
3. Banerjee, A.; Falvey, D. E. J. Org. Chem. 1997, 62, 6245-6251.
4. Hasan, A.; Stengele, K.-P.; Giegrich, H.; Cornwell, P.; Isham, K. R.; Sachleben, R. A.; Pfleiderer, W.; Foote, R. S. Tetrahedron 1997, 53, 4247-4264.
5. (e) Givens, R. S.; Jung, A.; Park, C.-H.; Weber, J.; Bartlett, W. J. Am. Chem. Soc. 1997, 119, 8369-8370.
6. (f) Gee, K. R.; Kueper, L. W., III Barnes, J.; Dudley, G.; Givens, R. S. J. Org. Chem. 1996, 61, 1228-1233.
7. (g) Jones, P. B.; Pollastri, M. P.; Porter, N. A. J. Org. Chem. 1996, 61, 9455-9461.
8. (h) Cameron, J. F.; Willson, C. G.; Fréchet, J. M. J. J. Am. Chem. Soc. 1996, 118, 12925-12937.
9. Schilling, M. L.; Katz, H. E.; Houlihan, F. M.; Kometani, J. M.; Stein, S. M.; Nalamasu, O. Macromolecules 1995, 28, 110-115.
10. (j) Pirrung, M. C.; Huang, C.-Y. Tetrahedron Lett 1995, 36, 5883-5884.
11. (k) Pirrung, M. C.; Shuey, S. W. J. Org. Chem. 1994, 59, 3890-3897.
12. Pirrung, M. C.; Lee, Y. R. J. Org. Chem. 1993, 58, 6961-6963.
13. Binkley, R. W.; Liu, X. J. Carbohydr. Chem. 1992, 11, 183-188.
14. (n) Liu, X. 1992, 450 pp.
15. (o) Pirrung, M. C.; Nunn, D. S. Bioorg. Med. Chem. Lett. 1992, 2, 1489-1492.
16. (p) Oliveira-Campos, A. M.; Queiroz, M. J. R. P.; Shannon, P. V. R. Chem. Ind. 1991, 352-353.
17. (q) Binkley, R. W.; Koholic, D. J. J. Org. Chem. 1989, 54, 3577-3581.
18. (r) Nishida, A.; Oishi, S.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 2266-2268.
19. (s) Masnovi, J.; Koholic, D. J.; Berki, R. J.; Binkley, R. W. J. Am. Chem. Soc. 1987, 709, 2851-2853.
20. (t) Haridasan, V. K.; Pillai, V. N. R. Proc. Indian Natl. Sci. Acad., Part A 1987, 53, 717-728.
21. (u) Rajasekharan Pillai, V. N. Org. Photochem. 1987, 9, 225-323.
22. Epling, G. A.; Walker, M. E. Tetrahedron Lett 1982, 23, 3843-3846.
23. (w) Ohtsuka, E.; Tanaka, S.; Ikehara, M.; Townsend, L. B.; Tipson, R. S. Nucleic Acid Chem. 1978, 1, 410-414.
24. Kalbag, S. M.; Roeske, R. W. J. Am. Chem. Soc. 1975, 97, 440-441.
25. (a) Aurell, M. J.; Boix, C.; Ceita, M. L.; Llopis, C.; Tortajada, A.; Mestrcs, R. J. Chem. Res., Synop. 1995, 452-453.
26. (b) Gravel, D.; Murray, S.; Ladouceur, G. J. Chem. Soc., Chem. Commun. 1985, 1828-1829.
27. Gravel, D.; Hebert, J.; Thoraval, D. Can. J. Chem. 1983, 61, 400-410.
28. Wilson, R. M.; Venkitachalam, S.; Layton, M.; Heckmann, J.; Barra, M.; Scaiano, J. C. In 10th Winter Conference of Inter-American Photochemical Society; LAPS: Clearwater Beach, FL, 1998; p C7.
29. (a) Schmittel, M.; Levis, M. Synlett 1996, 315-316.
30. (b) Tanemura, K.; Dohya, H.; Imamura, M.; Suzuki, T.; Horaguchi, T. Chem. Lett. 1994, 965-968.
31. Kamata, M.; Murakami, Y.; Tamagawa, Y.; Kato, M.; Hasegawa, E. Tetrahedron 1994, 50, 12821-12828.
32. Epling, G. A.; Wang, Q. Tetrahedron Lett. 1992, 33, 5909-5912.
33. (e) Epling, G. A.; Wang, Q. Synlett 1992, 335-336.
34. Corey, E. J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1965, 4, 1075-1077.
35. For a review, see: Gröbel, B.-T.; Seebach, D. Sythesis 1977, 357-402.
36. (a) Bookman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 720, 6542-6547.
37. (b) Sankararaman, S.; Ferner, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 6448.
38. Han, D. S.; Shine, H. J. J. Org. Chem. 1996, 61, 3977.
39. Penn, J. H.; Duncan, J. H. J. Org. Chem. 1993, 58, 2003-2008.
40. (e) Penn, J. H.; Lin, Z. J. Org. Chem. 1990, 55, 1554-1559.
41. (f) Penn, J. H.; Deng, D. L.; Aleshire, S. K J. Org. Chem. 1988, 53, 3572-3582.
42. (g) Popielarz, R.; Arnold, D. R. J. Am. Chem. Soc. 1990, 112, 3068-3082.
43. (h) Arnold, D. R.; Lamont, L. J. Can. J. Chem. 1989, 67, 2119-2127.
44. Okamoto, A.; Snow, M. S.; Arnold, D. R. Tetrahedron 1986, 42, 6175-6187.
45. (j) Gaillard, E. R.; Whitten, D. G. Ace. Chem. Res. 1996, 29, 292-297.
46. (k) Gan, H.; Leinhos, U.; Gould, I. R.; Whitten, D. G. J. Phys. Chem. 1995, 99, 3566-3573.
47. Kellett, M. A.; Whitten, D. G. Res. Chem. Intermed. 1995, 21, 587-611.
48. Leon, J. W.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 2226-2235.
49. (n) Whitten, D. G.; Kellett, M. A.; Leon, J.; Gan, H.; Tian, Z. W. Photochem. Photoelectrochem. Convers. Storage Sol. Energy, Proc. Int. Conf., 9th 1993, 257-275.
50. (o) Kellett, M. A.; Whitten, D. G. Mol. Cryst. Liq. Cryst. 1991, 194, 275-280.
51. (p) Ci, X.; Whitten, D. G. J. Am. Chem. Soc. 1989, 111, 3459-3461.
52. (q) Cl, X.; Whitten, D. G.; Fox, M. A.; Chanon, M. Photoinduced Electron Transfer 1988, Part C, 553-578.
53. (r) Lee, L. Y. G.; Ci, X.; Giannotti, C.; Whitten, D. G. J. Am. Chem. Soc. 1986, 108, 175-177.
54. (s) Maslak, P.; Chapman, W. H., Jr. J. Org. Chem. 1996, 61, 2647.
55. (t) Maslak, P.; Chapman, W. H., Jr.; Vallombroso, T. M.; Watson, B. A. J. Am. Chem. Soc. 1995, 777, 12380-12389.
56. (u) Maslak, P. Top. Curr. Chem. 1993, 168, 1.
57. Wang, Y.; Lucia, L. A.; Schanze, K. S. J. Phys. Chem. 1995, 99, 1961-1968.
58. (w) Burton, R. D.; Bartberger, M. D.; Zhang, Y.; Eyler, J. R.; Schanze, K S. J. Am. Chem. Soc. 1996, 118, 5655-5664.
59. Gravel, D.; Farmer, L.; Ayotte, C. Tetrahedron Lett 1990, 31, 63-66.
60. Gravel, D.; Farmer, L.; Denis, R. C.; Schultz, E. Tetrahedron Lett. 1994, 35, 8981-8984.
61. Roth, H. D.; Lamola, A. A. J. Am. Chem. Soc. 1974, 96, 6270-6275.
62. Glass, R. S.; Petsom, A.; Wilson, G. S. J. Org. Chem. 1986, 51, 4337-4342.
63. Ci, X.; Kellett, M. A.; Whitten, D. G. J. Am. Chem. Soc. 1991, 113, 3893-3904.
64. Yates, K.; Stewart, R. Can. J. Chem. 1959, 37, 664-671.
65. Extner, O. In Correlation Analysis in Chemistry; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1978; Chapter 10.
66. Stoweil, M. H. B.; Rock, R. S.; Rees, D. C.; Chan, S. I. Tetrahedron Lett. 1996, 37, 307-310.
67. Kessar, S. V.; Singh, T.; Vohra, R. Tetrahedron Lett. 1987, 28, 5323-5326.
68. Kessar, S. V.; Singh, T.; Vohra, R. Indian J. Chem. 1991, 30B, 999-1005.
69. As we tried to optimize the reaction yield, we found the following. Upon extended irradiation (over 4 h) GC-MS analysis of the reaction mixture showed a growing peak of a secondary photoproduct with a molecular ion of 272 and a fragmentation pattern consistent with the 4-formyltriphenylmethane structure. It is conceivable that under reaction conditions trityl alcohol 18 photochemically ionizes to produce the corresponding trityl cation, which is subsequently reduced to the triphenylmethane. We also cannot rule out a radical mechanism for such reduction.
70. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
71. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231-237.
72. The reaction with aldehydes was normally completed within 2 h. More hindered and/or aromatic ketones required 12+ h in the freezer to react.
73. Einborn, J.; Luche, J. L. J. Org. Chem. 1987, 52, 4124-4126.
74. Katzenellenbogen, J. A.; Bowlus, S. B. J. Org. Chem. 1973, 38, 627-632.
75. Bel-Rhlid, R.; Renard M. F.; Veschambre, H. Bull. Soc. Chim. Fr. 1996, 733, 1011-1021.
76. Guanti, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1986, 27, 3547-3550.
77. Watanabe, Y.; Ono, Y.; Hayashi, S.; Ucno, Y.; Toru, T. J. Chem. Soc., Perkin Trans, l 1996, 1879-1885.
78. Andersen, N. H.; McCrae, D. A.; Grotjahn, D. B.; Gabhe, S. Y.; Theodore, L. J.; Ippolito, R. M.; Sarkar, T. K. Tetrahedron 1981, 37, 4069-4079.