Novel photochemical hydrolysis of o-acetylphenylacetonitriles to amides

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3729-3732

  Lu, Qingyi ^a   Bovonsombat, Pakorn ^a   Agosta, William C ^a  

^a ROCKEFELLER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041634922     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952147s     Document Type: Article

References (17)

1. A preliminary communication has appeared: Lu, Q.; Bovonsombat, P.; Agosta, W. C. Tetrahedron Lett. 1995, 36, 8941.
2. 1H NMR spectrum of our sample of 4a was compatible with that on record.
3. Related cyclizations to 3-hydroxyisoquinolines have been studied: Jones, D. W. J. Chem. Soc. C 1969, 1729. For a relevant review, see: Hazai, L. Adv. Heterocycl. Chem. 1991, 52, 155.
4. Related cyclizations to 3-hydroxyisoquinolines have been studied: Jones, D. W. J. Chem. Soc. C 1969, 1729. For a relevant review, see: Hazai, L. Adv. Heterocycl. Chem. 1991, 52, 155.
5. Wagner, P. J. Pure Appl. Chem. 1977, 49, 259.
6. Biradical 5a presumably also relaxes to geometric isomers of 6a, and these then revert to 1a. For information on the distribution of enol isomers on γ-hydrogen abstraction in simple o-methylphenones, see: Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chem. Acta 1977, 60, 2595.
7. Wagner, P. J. Acc. Chem. Res. 1989, 22, 83, and references cited therein.
8. Risley, J. M.; DeFrees, S. A.; Van Etten, R. L. Org. Magn. Reson. 1983, 21, 28 and references cited therein.
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10. For a discussion of the factors that control hydrogen abstraction and its reversion in o-alkylphenones, see: Wagner, P. J.; Chen, C-P. J. Am. Chem. Soc. 1976, 98, 239. An additional limitation on the efficiency of reaction of 1a,b is the requirement that enol 6a,b be formed.
11. Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536.
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