Mechanism of Triazolinedione-Olefin Reactions. Ene and Cycloaddition

Journal of the American Chemical Society

Volumn 102, Issue 20, 1980, Pages 6384-6385

  Seymour, Catherine A ^a   Greene, Frederick D ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847086560     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00540a054     Document Type: Letter

References (15)

1. White, D. K.; Greene, F. D. J. Am. Chem. Soc. 1978, 100, 6760.
2. See: Burrage, M. E.; Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R. J. Chem. Soc., Perkin Trans. 2 1975, 1325, and references therein
3. See: Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
4. See: Gopalan, A.; Moercli, R.; Magnus, P. J. Chem. Soc., Chem. Commun. 1979, 548, and references therein
5. von Gustorf, E. K.; White, D. V.; Kim, B.; Hess, D.; Leitich, J. J. Org. Chem. 1970, 35, 1155.
6. Paste, D. J.; Chen, F-T. Tetrahedron Lett. 1973, 713.
7. Frimer, A. A. Chem. Rev. 1979, 79, 359.
8. Harding, L. B.; Goddard, W. A., III. J. Am. Chem. Soc. 1980, 102, 439.
9. Schulte-Elte, K. H.; Rautenstrauch, V. J. Am. Chem. Soc. 1980, 102, 1738.
10. Stephenson, L. M. Tetrahedron Lett. 1980, 21, 1005.
11. Grdina, B.; Orfanopoulos, M.; Stephenson, L. M. J. Am. Chem. Soc. 1979, 101, 3111.
12. An isolable species of known structure (X-ray analysis) and bearing some resemblance to 6a has been reported; l-(diphenylhydrazono)-3,5-di-oxo-4-phenyl-l,2,4-triazolidinium hydroxide, inner salt: Weidenborner, J. E.; Fahr, E.; Richter, M. J.; Koch, K.-H. Angew. Chem., Int. Ed. Engl 1973,12, 236.
13. For synthesis, see: McMurry, J. E.; Fleming, M. P.; Kees, K. L.; Krespi, L. R. J. Org. Chem. 1978, 43, 3255. For some reactions, see: Bolster, J.; Kellogg, R. M.; Meijer, E. W.; Wynberg, H. Tetrahedron Lett. 1979, 285, and references therein.
14. This might involve use of the lone pair of electrons of an azo nitrogen in the rate-determining step, in accord with formation of bromonium ion from olefin plus Br2.
15. Attention is also called to the difference in isotope effects observed in the ene reaction of dimethyl azodicarboxylate with