Mechanistic aspects of the formation of aldehydes and nitriles in photosensitized reactions of aldoxime ethers

Journal of Organic Chemistry

Volumn 72, Issue 11, 2007, Pages 4126-4134

  Peter De Lijser, H J ^a   Rangel, Natalie Ann ^a   Tetalman, Michelle A ^a   Tsai, Chao Kuan ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ETHERS; NITROGEN COMPOUNDS; NUCLEOPHILES; PHOTOOXIDATION; PHOTOSENSITIZERS;

ALDOXIME ETHERS; LASER FLASH PHOTOLYSIS; NITRILES; RADICAL CATIONS;

ALDEHYDES;

ACETONITRILE; ACETOPHENONE; ALDEHYDE; ALDOXIME; BENZALDEHYDE DERIVATIVE; CHLORANIL; HYDROGEN; NITRILE;

ARTICLE; ELECTRON TRANSPORT; ISOMERIZATION; PHOTOLYSIS; PHOTOOXIDATION; PHOTOSENSITIZATION; PROTON TRANSPORT; REACTION ANALYSIS;

ALDEHYDES; CHLORANIL; ETHERS; LASERS; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; OXIMES; PHOTOLYSIS;

EID: 34249802362     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0703707     Document Type: Article

References (73)

1. (a) Clement, J. G. Biochem. Pharmacol. 1982, 31, 1283.
2. (b) Dunn, M. A.; Siddell, F. R. JAMA, J. Am. Med. Assoc. 1989, 262, 649.
3. (c) Maxwell, D. M.; Lieske, C. N.; Brecht, K. M. Chem. Res. Toxicol. 1994, 7, 428.
4. (d) Kwong, T. C. Ther. Drug Monit. 2002, 24, 144.
5. (e) Baigar, J. Acta Med. 1996, 39, 101.
6. (a) Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, A. J. Chem. Rev. 2002, 102, 1091.
7. (b) Rosen, G. M.; Tsai, P.; Pou, S. Chem. Rev. 2002, 102, 1191.
8. (c) Koikov, L. N.; Alexeeva, N. V.; Lisitza, E. A.; Krichevsky, E. S.; Grigoryev, N. B.; Danilov, A. V.; Severina, I. S.; Pyatakova, N. V.; Granik, V. G. Mendeleev Commun. 1998, 165.
9. (d) Jousserandor, A.; Boucher, J.-L.; Henry, Y.; Niklaus, B.; Clement, B.; Mansuy, D. Biochemistry 1998, 37, 17179.
10. (e) Kato, M.; Nishino, S.; Ohno, M.; Fukuyama, S.; Kita, Y.; Hirasawa, Y.; Nakanishi, I.; Takasugi, H.; Sakane, K. Bioorg. Med. Chem. Lett. 1996, 6, 33.
11. (f) Decout, J.-L.; Roy, B.; Fontecave, M.; Muller, J.-C.; Williams, P. H.; Loyaux, D. Bioorg. Med. Chem. Lett. 1995, 5, 973.
12. (g) Kita, Y.; Hirasawa, Y.; Maeda, K.; Nishio, M.; Yoshida, K. Eur. J. Pharmacol. 1994, 257, 123.
13. (h) Isono, T.; Koibuchi Y.; Sato, N.; Fumichi, A.; Nishii, M.; Yamamoto, T.; Mori, J.; Kohsaka M.; Ohtsuka, M. Eur. J. Pharmacol. 1993, 246, 205.
14. Milne, G. W. A. CRC Handbook of Pesticides; CRC Press: Boca Raton, 1995.
15. Halford, B. Chem. Eng. News 2005, 83, 10.
16. Rhodes, C. J. Toxicology of the Human Environment; Taylor & Francis: New York, 2000.
17. (a) Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611.
18. (b) Wrighton, S. A.; Schuetz, E. G.; Thummel, K. E.; Shen, D. D.; Korzekwa, K. R.; Watkins, P. B. Drug Metab. Rev. 2000, 32, 339.
19. Guengerich, F. P. In Cytochromes P450: Metabolic and Toxicological Aspects; Ioannides, C., Ed., CRC Press: Boca Raton, 1996; p 55.
20. (a) Everett, S. A.; Naylor, M. A.; Stratford, M. R. L.; Patel, K. B.; Ford, E.; Mortensen, A.; Ferguson, A. C.; Vojnovic, B.; Wardman, P. J. Chem. Soc., Perkin Trans. 2001, 1989.
21. (b) Benchariff, L.; Tallec, A.; Tardivel, R. Electrochim. Acta 1997, 42, 3509.
22. (c) Rhodes, C. J.; Agirbas, H. J. Chem. Soc. Faraday Trans. 1990, 86, 3303.
23. (d) Horne, D. G.; Norrish, R. G. W. Proc. Roy. Soc. Lond. A 1970, 315, 287.
24. (e) Edge, D. J.; Norman, R. O. C. J. Chem. Soc. (B) 1969, 182.
25. (f) Smith, P.; Fox, W. M. Can. J. Chem. 1969, 47, 2227.
26. (g) Adams, J. Q. J. Am. Chem. Soc. 1967, 89, 6022.
27. (a) de Lijser, H. J. P.; Fardoun, F. H.; Sawyer, J. R.; Quant, M. Org. Lett. 2002, 4, 2325.
28. (b) de Lijser, H. J. P.; Kim, J. S.; McGrorty, S. M.; Ulloa, E. M. Can. J. Chem. 2003, 81, 575.
29. (c) de Lijser, H. J. P.; Tsai, C.-K. J. Org. Chem. 2004, 69, 3057.
30. (d) Park, A.; Kim, J. S.; Kosareff, N. M.; de Lijser, H. J. P. Photochem. Photobiol. 2006, 82, 110.
31. (e) de Lijser, H. J. P.; Hsu, S.; Marquez, B. V.; Park, A.; Sanguantrakun, N.; Sawyer, J. R. J. Org. Chem. 2006, 71, 7785.
32. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: Oxford, 1999.
33. (a) Cai, T.; Xian, M.; Wang, P. G. Bioorg. Med. Chem. Lett. 2002, 12, 1507.
34. (b) Sanakis, Y.; Goussias, C.; Mason, R. P.; Petrouleas, V. Biochemistry 1997, 36, 1411.
35. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
36. (a) Bockman, T. M.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1996, 1633.
37. (b) Jones, G., II; Mouli, N.; Haney, W. A.; Bergmark, W. R. J. Am. Chem. Soc. 1997, 119, 8788.
38. (a) Bordwell, F. G.; Ji, G.-Z. J. Org. Chem. 1992, 57, 3019.
39. (b) Bordwell, F. G.; Zhang, X.-M.; Satish, A. V.; Cheng, J.-P. J. Am. Chem. Soc. 1994, 116, 6605.
40. (c) Bordwell, F. G.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 4858.
41. (d) Bordwell, F. G.; Zhao, Y.; Cheng, J.-P. J. Phys. Org. Chem. 1998, 11, 10.
42. Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290.
43. (a) Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462.
44. (b) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc 1993, 115, 366.
45. (c) Dinnocenzo, J. P.; Simpson, T. R.; Zuilhof, H.; Todd, W. P.; Heinrich, T. J. Am. Chem. Soc. 1997, 119, 987.
46. (d) Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 119, 1876.
47. (e) de Lijser, H. J. P.; Snelgrove, D. W.; Dinnocenzo, J. P. J. Am. Chem. Soc. 2001, 123, 9698.
48. (a) Padwa, A.; Albrecht, F. J. Am. Chem. Soc. 1972, 94, 1000.
49. (b) Padwa, A.; Albrecht, F. J. Am. Chem. Soc. 1974, 96, 4849.
50. (c) Padwa, A.; Albrecht, F. J. Org. Chem. 1974, 39, 2361.
51. (d) Padwa, A. Chem. Rev. 1977, 77, 37.
52. (e) Rico, I.; Maurette, M. T.; Oliveros, E.; Riviere, M.; Lattes, A. Tetrahedron 1980, 36, 1779.
53. (f) Takeda, Y.; Misawa, H.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc Jpn. 1989, 62, 2213.
54. (g) Furuuchi, H.; Arai, T.; Sakuragi, H.; Tokumaru, K. J. Phys. Chem. 1991, 95, 10322.
55. (h) Arai, T.; Furuya, Y.; Furuuchi, H.; Tokumaru, K. Chem. Phys. Lett. 1993, 212, 597.
56. (i) Lalevée, J.; Allonas, X.; Louërat, F.; Fouassier, J. P.; Tachi, H.; Izumitani, A.; Shirai, M.; Tsunooka, M. Phys. Chem. Chem. Phys. 2001, 3, 2721.
57. (j) Lalevée, J.; Allonas, X.; Louërat, F.; Fouassier, J. P. J. Phys. Chem. A 2002, 106, 6702.
58. de Lijser, H. J. P.; Rangel, N. A. J. Org. Chem. 2004, 69, 8315.
59. Pratt, D. A.; Blake, J. A.; Mulder, P.; Walton, J. C.; Korth, H.-G.; Ingold, K. U. J. Am. Chem. Soc. 2004, 126, 10667.
60. Recent experiments in our laboratory suggest that the iminyl C-H bond is indeed weaker than the α-C-H bond. Chlorination of O-alkyl benzaldehyde oximes with N-chlorosuccinimide proceeds selectively and results in the formation of the corresponding N-alkoxy iminoyl chlorides; no chlorination at the α-carbon is observed.
61. (a) Corey, E. J.; Petrzilka, M.; Ueda, Y. Helv. Chim. Acta 1977, 60, 2294.
62. (b) Ensley, H. E.; Lohr, R. Tetrahedron Lett. 1978, 19, 1415.
63. (c) Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755.
64. (d) Geno, M. J. K.; Dawson, J. H. Inorg. Chem. 1984, 23, 509.
65. (e) McCarroll, A. J.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 2000, 1868.
66. (f) Di Gioia, M. L.; Leggio, A.; Le Pera, A.; Liguori, A.; Siciliano, C. J. Org. Chem. 2005, 70, 10494.
67. Herkstroeter, W. G.; Gould, I. R. in: Physical Methods of Chemistry Series, 2nd ed.; Rossiter, B.; Baetzold, R. Eds.; Wiley: New York, 1993; Vol. 8, p 225.
68. Lorance, E. D.; Kramer, W. H.; Gould, I. R. J. Am. Chem. Soc. 2002, 124, 15225.
69. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
70. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
71. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
72. Spartan '04, Wavefunction, Inc., Irvine CA.
73. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley and Sons: New York, 1986.