Photo-Aza-Claisen Rearrangements of Cyclic Enaminones

Journal of Organic Chemistry

Volumn 54, Issue 17, 1989, Pages 4165-4168

  Vogler, B ^a   Bayer, R ^a   Meller, M ^a   Kraus, W ^a   Schell, Fred M ^b  

^a UNIVERSITY OF HOHENHEIM   (Germany)

^b UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001222330     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00278a033     Document Type: Article

References (17)

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2. Oppolzer, W. Acc. Chem. Res. 1982, 15, 135.
3. Recently an example was reported where the ene product is the main product. Berry, N. M.; Darey, M. C. P.; Harwood, L. M. Tetrahedron Lett. 1986, 27, 2319.
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11. Oppolzer, W.; Bird, T. G. C. Helv. Chim. Acta 1979, 62, 1199.
12. Schell, F. M.; Cook, P. M. J. Org. Chem. 1984, 49, 4067. (b) For another example of intramolecular cycloaddition of a vinylogous amide, see: Winkler, J. D.; Hershberger, P. M.; Springer, J. P. Tetrahedron Lett. 1986, 27, 5177.
13. Wolff, S.; Agosta, W. C. J. Am. Chem. Soc. 1983,105,1292,1299.
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15. Lutz, R. P. Chem. Rev. 1984, 84, 205. For certainty the starting material was also heated to reflux in benzene, whereas the photochemistry was performed at 16 °C. No thermal rearrangement was detectable.
16. An analogous photo-Claisen rearrangement is reported by Smith, A. B., III; Agosta, W. C. J. Am. Chem. Soc. 1973, 95, 1961.
17. Hanck, M.; Schneider, H. J. Justus Liebigs Ann. Chem. 1965, 686, 16.