Air oxidation of 2-aryl-1-tetralones in basic, neutral, and acidic media: An unprecedented oxidative aryl migration to 2-aryloxy-1-naphthols under acidic condition

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5691-5695

  Ishikawa, Tsutomu ^a   Hino, Keiko ^a   Yoneda, Takaaki ^a   Murota, Masayuki ^a   Yamaguchi, Kentaro ^a   Watanabe, Toshiko ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL DERIVATIVE; BENZOPHENANTHRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033597806     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9824854     Document Type: Article

References (25)

1. Ishii, H.; Ishikawa, T.; Takeda, S.; Suzuki, M.; Harayama, T. Chem. Pharm. Bull. 1992, 40, 2002-2006 and references therein.
2. Ishikawa, T.; Murota, M.; Watanabe, T.; Harayama, T.; Ishii, H. Tetrahedron Lett. 1995, 36, 4269-4271.
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5. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M.; Harayama, T. Chem. Pharm. Bull. 1990, 38, 1775-1777.
6. For example, see: Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361-3364. We have also observed the effectively of CsF as a base in some organic reactions: Ishikawa, T.; Mizutani, A.; Miwa, C.; Oku, Y.; Komano, N.; Takami, A.; Watanabe, T. Heterocycles 1997, 45, 2261-2272. Ishikawa, T.; Oku, Y.; Kotake, K-I.; Ishii, H. J. Org. Chem. 1996, 67, 6484-6485. Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371-380. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
7. For example, see: Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361-3364. We have also observed the effectively of CsF as a base in some organic reactions: Ishikawa, T.; Mizutani, A.; Miwa, C.; Oku, Y.; Komano, N.; Takami, A.; Watanabe, T. Heterocycles 1997, 45, 2261-2272. Ishikawa, T.; Oku, Y.; Kotake, K-I.; Ishii, H. J. Org. Chem. 1996, 67, 6484-6485. Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371-380. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
8. For example, see: Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361-3364. We have also observed the effectively of CsF as a base in some organic reactions: Ishikawa, T.; Mizutani, A.; Miwa, C.; Oku, Y.; Komano, N.; Takami, A.; Watanabe, T. Heterocycles 1997, 45, 2261-2272. Ishikawa, T.; Oku, Y.; Kotake, K-I.; Ishii, H. J. Org. Chem. 1996, 67, 6484-6485. Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371-380. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
9. For example, see: Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361-3364. We have also observed the effectively of CsF as a base in some organic reactions: Ishikawa, T.; Mizutani, A.; Miwa, C.; Oku, Y.; Komano, N.; Takami, A.; Watanabe, T. Heterocycles 1997, 45, 2261-2272. Ishikawa, T.; Oku, Y.; Kotake, K-I.; Ishii, H. J. Org. Chem. 1996, 67, 6484-6485. Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371-380. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
10. For example, see: Clark, J. H.; Holland, H. L.; Miller, J. M. Tetrahedron Lett. 1976, 3361-3364. We have also observed the effectively of CsF as a base in some organic reactions: Ishikawa, T.; Mizutani, A.; Miwa, C.; Oku, Y.; Komano, N.; Takami, A.; Watanabe, T. Heterocycles 1997, 45, 2261-2272. Ishikawa, T.; Oku, Y.; Kotake, K-I.; Ishii, H. J. Org. Chem. 1996, 67, 6484-6485. Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371-380. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
11. For example, see: Kuwajima, I.; Murofushi, T.; Nakamura, E. Synthesis 1976, 602-604.
12. We have examined basic air-oxidation using various weak bases including CsF. The results will be reported elsewhere.
13. Ishii, H.; Kawanabe, E.; Harada, K.-I.; Deushi, T.; Ueda, E.; Watanabe, T.; Ichikawa, Y.-I.; Sakamoto, M.; Ishida, T.; Takahashi, T.; Nakajima, K.; Ishikawa, T. Chem. Pharm. Bull. 1983, 31, 3039-3055.
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15. 2 scavenger under this condition.
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20. To simplify the discussion, additional pathways and intermediates, arising from hydration of the ketone carbonyls of 3 and 8, are excluded from the proposed mechanism in Scheme 5.
21. It is known that endoperoxides generate light during their concerted decomposition under basic conditions. Although no chemical luminescence was observed in our reactions, we supposed the pathway through endoperoxides 9 as a possible route because of different acidic condition used in our case.
22. Ogata et al. reported the acyclic mechanism such as path D in Scheme 5 for the alkaline decomposition of α-hydroperoxy ketones as a main path, but alternative cyclic one such as path C in Scheme 5 was also suggested by other group (Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc. 1976, 97, 6983-6989 and references therein).
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