Thermodynamic parameters ΔΔH# and ΔΔS# as probes for the transition state in the reaction of N-phenyltriazolinedione with alkenes in nucleophilic solvents

Tetrahedron Letters

Volumn 47, Issue 17, 2006, Pages 2961-2964

  Syrgiannis, Zois ^a   Elemes, Yiannis ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Ene reactions; Solvent addition; Thermodynamic parameters; Triazolinediones

Indexed keywords

2 METHYL 2 BUTENE; ALCOHOL; ALKENE; AZIRIDINE DERIVATIVE; AZIRIDINIUM IMIDE; BENZENE DERIVATIVE; BUTANE; N PHENYLTRIAZOLINEDIONE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; DEUTERON NUCLEAR MAGNETIC RESONANCE; ENTROPY; GAS CHROMATOGRAPHY; THERMODYNAMICS;

EID: 33645240059     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.099     Document Type: Article

References (34)

1. H.M.R. Hoffman Angew. Chem., Int. Ed. Engl. 8 1969 556 577
2. W.H. Pirkle, and J.C. Stickler J. Chem. Soc., Chem. Commun. 1967 760 761
3. S. Ohashi, K.W. Leong, K. Matyjaszewski, and G.B. Butler J. Org. Chem. 45 1980 3467 3471
4. S. Ohashi, and G.B. Butler J. Org. Chem. 45 1980 3472 3476
5. 2 1979 Academic Press New York 287 429
6. 2 1985 CRC Press Boca Raton, FL 68 87
7. 2 1985 CRC Press Boca Raton, FL 205 272
8. W. Adam, N. Bottke, O. Krebs, and B. Engels J. Am. Chem. Soc. 123 2001 5542 5548
9. E.J. Corey, and B.B. Snider Tetrahedron Lett. 14 1973 3091 3094
10. W. Adam, and A. Griesbeck Angew. Chem., Int. Ed. Engl. 24 1985 1070 1071
11. W. Adam, and B. Nestler Liebigs Ann. Chem. 1990 1051 1053
12. C.J. Moody Adv. Heterocycl. Chem. 30 1982 1 45
13. S. Radl Adv. Heterocycl. Chem. 67 1996 119 205
14. M. Orfanopoulos, M. Stratakis, and Y. Elemes Tetrahedron Lett. 30 1989 4875 4879
15. Y. Elemes, M. Stratakis, and M. Orfanopoulos Tetrahedron Lett. 30 1989 6903 6906
16. E.L. Clennan, X. Chen, and J.J. Koola J. Am. Chem. Soc. 112 1990 5193 5199
17. S. Yamada, K. Hamano, and M. Shimizu Tetrahedron Lett. 32 1991 2379 2382
18. W. Adam, N. Bottke, and O. Krebs Org. Lett. 2 2000 3293 3296
19. G.C. Vougioukalakis, and M. Orfanopoulos Synlett 2005 713 731
20. M. Stratakis, and M. Orfanopoulos Tetrahedron 56 2000 1595 1615
21. W. Adam, and O. Krebs Chem. Rev. 103 2003 4131 4146
22. L.M. Stephenson, M.J. Grdina, and M. Orfanopoulos Acc. Chem. Res. 13 1980 419 425
23. C.A. Seymour, and F.D. Greene J. Org. Chem. 47 1982 5226 5227
24. C.C. Cheng, C.A. Seymour, M.A. Petty, F.D. Greene, and J.F. Blound J. Org. Chem. 49 1984 2910 2916
25. M. Orfanopoulos, C.S. Foote, and I. Smonou Tetrahedron Lett. 28 1987 15 18
26. Y. Elemes, and C.S. Foote J. Am. Chem. Soc. 114 1992 6044 6050
27. W. Adam, O. Krebs, M. Orfanopoulos, M. Stratakis, and G.C. Vougioukalakis J. Org. Chem. 68 2002 2420 2425
28. D.A. Singleton, and C. Hang J. Am. Chem. Soc. 121 1999 11885 11893
29. M. Stratakis, M. Hatzimarinaki, G.E. Froudakis, and M. Orfanopoulos J. Org. Chem. 66 2001 3682 3687
30. G. Vassilikogiannakis, Y. Elemes, and M. Orfanopoulos J. Am. Chem. Soc. 122 2000 9540 9541
31. Y. Elemes, and M. Orfanopoulos Tetrahedron Lett. 32 1991 2667 2670
32. 3: C, 60.63; H, 6.91; N, 15.15. Found: C, 60.71; H, 6.92; N, 15.13.
33. This inductive effect though is in favor of the addition of the first solvent molecule to the tertiary carbon atom.
34. Such low organization is valid also for the first interacting molecule in the case of a bulky solvent.