Solvent dependent photochemical reactions of 3-(2-alkylphenyl)-2,2- dimethyl-3-oxopropanoates and their related compounds

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 9013-9018

  Saito, Masaichi ^a   Kamei, Yumiko ^a   Kuribara, Kanae ^a   Yoshioka, Michikazu ^a   Hasegawa, Tadashi ^b  

^a SAITAMA UNIVERSITY   (Japan)

^b TOKYO GAKUGEI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; DIENESTROL; HEXANE; METHANOL; NAPHTHALENE DERIVATIVE; OXYGEN; PEROXIDE; PROPIONIC ACID DERIVATIVE; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; IRRADIATION; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031789010     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981433b     Document Type: Article

References (38)

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24. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
25. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
26. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
27. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
28. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
29. For example, see: (a) Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597. (b) Lutz, H.; Breheret, E.; Lindqvist, L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 2096. (c) Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Faraday Trans. 1 1976, 72, 1096. (d) Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595. (e) Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1977, 99, 7713. (f) Viriot-Villaume, M.-L.; Carré, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 1395. (g) Carré, M.-L.; Viriot-Villaume, M.-L.; Caubère, P. J. Chem. Soc., Perkin Trans. 1 1979, 2542.
30. We have already reported similar photochemical reactions in the presence of oxygen, see: Yoshioka, M.; Nishizawa, K.; Suzuki, J.; Iwata, Y.; Kumakura, S.; Hasegawa, T. J. Chem. Soc., Perkin Trans. 1 1995, 3097.
31. In the absence of light, dienols derived from benzocyclobutenols by heating are known to react with oxygen, (a) Yang, N. C.; Rivas, C. J. Am. Chem. Soc. 1981, 83, 2213. (b) Heindel, N. D.; Sarver, E. W.; Pfau, M. Tetrahedron Lett. 1968, 3579. Porter, G.; Tchir, M. F. J. Chem. Soc. A 1971, 3772. Pfau, M.; Sarver, E. W.; Heindel. N. D. Bull. Soc. Chim. Fr. 1973, 183.
32. In the absence of light, dienols derived from benzocyclobutenols by heating are known to react with oxygen, (a) Yang, N. C.; Rivas, C. J. Am. Chem. Soc. 1981, 83, 2213. (b) Heindel, N. D.; Sarver, E. W.; Pfau, M. Tetrahedron Lett. 1968, 3579. Porter, G.; Tchir, M. F. J. Chem. Soc. A 1971, 3772. Pfau, M.; Sarver, E. W.; Heindel. N. D. Bull. Soc. Chim. Fr. 1973, 183.
33. In the absence of light, dienols derived from benzocyclobutenols by heating are known to react with oxygen, (a) Yang, N. C.; Rivas, C. J. Am. Chem. Soc. 1981, 83, 2213. (b) Heindel, N. D.; Sarver, E. W.; Pfau, M. Tetrahedron Lett. 1968, 3579. (c) Porter, G.; Tchir, M. F. J. Chem. Soc. A 1971, 3772. Pfau, M.; Sarver, E. W.; Heindel. N. D. Bull. Soc. Chim. Fr. 1973, 183.
34. In the absence of light, dienols derived from benzocyclobutenols by heating are known to react with oxygen, (a) Yang, N. C.; Rivas, C. J. Am. Chem. Soc. 1981, 83, 2213. (b) Heindel, N. D.; Sarver, E. W.; Pfau, M. Tetrahedron Lett. 1968, 3579. Porter, G.; Tchir, M. F. J. Chem. Soc. A 1971, 3772. (d) Pfau, M.; Sarver, E. W.; Heindel. N. D. Bull. Soc. Chim. Fr. 1973, 183.
35. For example, see: Ito, Y.; Matsuura, T. J. Am. Chem. Soc. 1883, 105, 5237, and references therein.
36. The photochemical reactions of N,N-disubstituted benzoyl-acetamide, see: (a) Hasegawa, T.; Aoyama, H.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2054. (b) Hasegawa, T.; Aoyama, H.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1979, 963.
37. The photochemical reactions of N,N-disubstituted benzoyl-acetamide, see: (a) Hasegawa, T.; Aoyama, H.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1976, 2054. (b) Hasegawa, T.; Aoyama, H.; Omote, Y. J. Chem. Soc., Perkin Trans. 1 1979, 963.
38. Vollmar, A.; Dunn, M. S. J. Org. Chem. 1960, 25, 387.