Regio- and Stereoselectivity in the Ene Reaction of N-Phenyl-l,2,4-triazoline-3,5-dione with, α,β-Unsaturated Carbonyl Substrates

Journal of Organic Chemistry

Volumn 45, Issue 22, 1980, Pages 4287-4292

  Bottorff, Kyle J ^a   Hoye, Thomas R ^a   Caruso, Andrew J ^a   Dellarialb, Joseph F ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002656875     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01310a007     Document Type: Article

References (15)

1. Lando Fellow, University of Minnesota, Summer 1978.
2. Dissertation Fellow, University of Minnesota, 1980-81.
3. Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969,8, 566.
4. Conia, J. M.; LePerchec, P. Synthesis 1975, 1.
5. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
6. Shiloff, J. D.; Hunter, N. R. Tetrahedron Lett. 1976, 3773. We thank Professor Hunter for an exchange of information regarding his further study of this reaction.
7. Denny, R. W.; Nickon, A. Org. React. 1973, 20, Chapter 2.
8. Gopalan, A.; Moerck, R.; Magnus, P. J. Chem. Soc., Chem. Commun. 1979,548.
9. Ohashi, S.; Leong, K.; Matyjaszewski, K.; Butler, G. B. J. Org. Chem. 1980, 45, 3467; Ohashi, S.; Butler, G. B. J. Chem. Soc., Chem. Commun. 1980, 45, 3472.
10. Ensley, H. E.; Carr, R. V. C. Tetrahedron Lett. 1977,513. Enaley, H. E.; Carr, R. V. C.; Martin, R. S.; Pierce, T. E. J. Am. Chem. Soc. 1980, 102, 2836.
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14. Hunt, B. J.; Rigby, W, Chem. Ind. (London) 1967, 1868.
15. In our hands the preparation of PTAD by nitrogen tetroxide oxidation (Stickler, J. C.; Pirkle, W. H. J. Org. Chem. 1966, 31, 3444) proved to be more efficient and was easier to perform than the tert-butyl hypochlorite method (Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R.; Watts, C. T. Org. Synth. 1971, 51, 121).