Remote ε-secondary isotope effect in the reaction of tetracyanoethylene with 2,5-dimethyl-2,4-hexadiene. A step-wise mechanism

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3075-3078

  Vassilikogiannakis, Georgios ^a   Orfanopoulos, Michael ^a  

^a UNIVERSITY OF CRETE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029937880     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00473-X     Document Type: Article

References (21)

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2. b) ibid 1987, 959-78.
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4. b) Huisgen, R. Acc. Chem. Res. 1977, 199-206.
5. c) ibid, 117-24.
6. d) Clennan, E. L.; Lewis, K. K. J. Am. Chem. Soc. 1987, 109, 2475-78.
7. e) Gotoh, T.; Padias, A. B.; Hall, H. K. Jr. J. Am. Chem. Soc. 1986, 108, 4920-31.
8. f) Kim, T.; Sarker, H.; Bauld, N. L. J. Chem. Soc. Perkin Trans. II 1995, 577-80.
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14. O'Shea, K. E.; Foote, C. S. Tetrahedron Lett. 1990, 31, 841-44.
15. 6= calcd 116.1472, found 116.1458.
16. Frey, J. E.; Andrews, A. M.; Ankoviac, D. G.; Beaman, D. N.; Du Pont L. E.; Elsner, T. E.; Lang, S. R.; Oosterbaan Zwart, M. A.; Seagle, R. E.; Torreano, L. A. J. Org. Chem. 1990, 55, 606-24.
17. 3 to the reaction mixture and then acidification of the aqueous layer with IN HCl.
18. a) Bartell, L. S. J. Am. Chem. Soc. 1961, 83, 3567-71.
19. b) Karabatsos, G. J.; Sonnichsen, G. C.; Papaioannou, C. G.; Scheppele, S. E.; Shone, R. L. J. Am. Chem. Soc. 1967, 90, 463-65.
20. Carpenter, K. B. Determination of Organic Reaction Mechanisms, John Wiley, 1984.
21. Shiner, V. J.; Kritz, G. S.; J. Am. Chem. Soc. 1964, 87, 2643-45.