Kinetic study of thermal 1, 3-dipolar cycloaddition of azomethine ylides by using differential scanning calorimetry

ChemPlusChem

Volumn 77, Issue 9, 2012, Pages 770-777

  Mancebo Aracil, Juan ^a   Muñoz Guillena, Marfa J ^a   Such Basáñez, Ion ^a   Sansano Gil, Jose M ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Autocatalysis; Azomethine ylides; Cycloaddition; Differential scanning calorimetry; Kinetics

Indexed keywords

EID: 84869001482     PISSN: None     EISSN: 21926506     Source Type: Journal    
DOI: 10.1002/cplu.201200107     Document Type: Article

References (56)

1. a) Comprehensive Handbook of Calorimetry and Thermal Analysis (Ed.: M. Sorai), Wiley, Chichester, 2004;
2. b) Handbook of Thermal Analysis and Calorimetry, Vol. 1-5 (Ed.: P. K. Gallagher), Elsevier Science, Amsterdam, 2003-2007;
3. c)Principles and Applications of Thermal Analysis (Ed.: P. Gabbot), Blackwell Publishing, Oxford, 2008;
4. d) Differential Scanning Calorimetry (Eds.: G. Höhne, W. F. Hemminger, H.-J. Flammersheim), Springer, Heidelberg, 2010;
5. e) Modulated Temperature Differntial Scanning Calorimetry: Theoretical and Practical Applications in Polymer Characterization (Hot Topics in Thermal Analysis and Calorimetry) (Eds.: M. Reading, D.J. Hourston), Springer, Dordretch, 2010.
6. T. F. J. Pjpers, V. B. F. Mathot, B. Goderis, R. L. Scherrenberg, E. W. van der Vegte, Macromolecules 2002, 35, 3601-3613.
7. Thermal Analysis UserCom Series, Mettler Toledo Inc. Publishing, 1995-2012.
8. a) K. A. Connors, Chemical Kinetics, The Study of Reaction Rates in Solution, VCH Publishers, New York, 1990;
9. b)R. I. Masel, Chemical Kinetics and Catalysis, Wiley, New York, 2001;
10. c) M. R. Wright, An Introduction to Chemical Kinetics, Wiley, Chichester, 2004.
11. See reference [1 b], Vol. 1, pp. 147-224.
12. The activation energy of the Diels-Alder reaction between hexachloro-cyclopentadiene and cyclopentene was reported by using an excess of hexachlorocyclopentadiene and assuming pseudo first-order kinetics: J. A. Belichmeiera, H. K. Cammenga, P. B. Schneiderb, A. G. Steerb, Ther-mochim. Acta 1998, 310, 147-151.
13. R. Huisgen, Angew. Chem. 1963, 75, 604-637;
14. Angew. Chem. Int. Ed. Engl. 1963, 2, 565-632.
15. For recent computational studies concerning 1, 3-DC of azomethine ylides, see: a)T K. Das, M. Banerjee, J. Phys. Org. Chem. 2010, 23, 148-155;
16. b) L. R. Domingo, E. Chamorro, P. Pérez, Lett. Org. Chem. 2010, 7, 432-439;
17. c) A. de Cózar, F. P. Cossío, Phys. Chem. Chem. Phys. 2011, 13, 10858-10868, and references therein.
18. For general reviews describing wide applications of 1, 3-DC of azomethine ylides, see: a)Synthetic Applications of 1, 3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), Wiley, New Jersey, 2003
19. b)C. Nájera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105-1150;
20. c)W. Eberbach, Sci. Synth. 2004, 27, 441-498;
21. d) I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765-2809;
22. V Nair, T D. Suja, Tetrahedron 2007, 63, 12247-12275;
23. f) A. Padwa, S. K. Bur, Tetrahedron 2007, 63, 5341-5378.
24. The enantioselective 1, 3-DC of azomethine ylides is a prolific area in organic synthesis and has been reviewed frequently. For selected recent examples, see: a)H. Pellissier, Tetrahedron 2007, 63, 3235-3285;
25. b)C. Nájera, J. M. Sansano in Topics in Heterocyclic Chemistry, Vol. 12 (Ed.: A. Hassner), Springer, Berlin-Heidelberg, 2008, pp. 117-145;
26. c) L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887-2902;
27. d) M. Álvarez-Corral, M. Muñoz-Dorado, I. Rodríguez-García, Chem. Rev. 2008, 108, 3174-3198;
28. e) M. Naodovic, H. Yamamoto, Chem. Rev. 2008, 108, 3132-3148;
29. f) C. Nájera, J. M. Sansano, M. Yus, J. Braz. Chem. Soc. 2010, 21, 377-412;
30. g) M. Kissane, A. R. Maguire, Chem. Soc. Rev. 2010, 39, 845-883;
31. h)J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784-6794.
32. The 1, 3-DC of azomethine ylides with imines (including self-cycloaddition in the absence of a trapping agent) has been employed in the synthesis of α,β-dehydro-α-amino acid derivatives: a) P. W. Groundwater, T. Sharif, A. Arany, D. E. Hibbs, M. B. Hursthouse, M. Nyerges, Tetrahedron Lett. 1998, 39, 1433-1436;
33. b) P. W. Groundwater, T. Sharif, A. Arany, D. E. Hibbs, M. B. Hursthouse, I. Garnett, M. Nyerges, J. Chem. Soc. Perkin Trans. 1 1998, 2837-2846.
34. See for example: a)S. Jacquot-Rousseau, G. Schmitt, A. Khatyr, M. Knorr, M. M. Kubicki, E. Vigier, O. Blacque, Eur. J. Org. Chem. 2006, 1555-1562;
35. b) P. Elo, A. Parssinen, M. Nieger, M. Leskela, T. Repo, J. Organomet. Chem. 2009, 694, 2927-2933.
36. Fast and accurate algorithm for the simulation of NMR spectra of large spin systems can be performed: A. M. Castillo, L. Patiny, J. Wist, J. Magn. Reson. 2011, 209, 123-133.
37. K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074.
38. There are not many examples in the literature concerning the kinetics of 1, 3-DC involving azomethine ylides: K. Elender, P. Riebel, A. Weber, J. Sauer, Tetrahedron 2000, 56, 4261-4265.
39. Handbook of Thermal Analysis (Eds.: T. Hatakeyama, Z. Liu), Wiley, New York, 1998, Chapter 4.
40. F. Mata-Perez, J. Pérez-Benito, J. Chem. Educ. 1987, 64, 925-927.
41. a)TA-073, TA Instruments, http://www.tainst.com;
42. b)TA-143A, TA Instruments, http://www.tainst.com.
43. H. E. Kissinger, Anal. Chem. 1957, 29, 1702-1706.
44. H. J. Borchardt, F. Daniels, J. Am. Chem. Soc. 1957, 79, 41-46.
45. a)T J. Ozawa, Therm. Anal. 1970, 2, 301-324;
46. b) J. H. Flynn, L. A. Wall, J. Res. Nat. Bur. Stand 1966, 70A, 487-493.
47. a)Z.-H. Chen, F.-Q. Zu, X.-F. Li, J. Yu, Y. Xi, R.-R. Shen, J. Phys. Condens. Matter 2007, 19, 116106;
48. b)S. Matecic-Musanic, I. Fiamengo-Houra, M. Suceska, Cent. Eur. J. Energ. Mater. 2010, 7, 233-251.
49. J. Farjas, N. Butchosa, P. Roura, J. Therm. Anal. Calorim. 2010, 102, 615-625.
50. P. E. Sánchez-Jiménez, J. M. Criado, A. Pérez-Maqueda, J. Therm. Anal. Calorim. 2008, 94, 427-432.
51. ASTM E698-11, ASTM Int., West Conshohocken, US.
52. See the Supporting Information.
53. ASTM E2070-00, ASTM Int., West Conshohocken, US.
54. MLR was performed using the solver application tool of Microsoft Excel (Office 2007).
55. J. Wang, M.-P. G. Laboire, M. P. Wolcott, J. Appl. Polym. Sci. 2007, 105, 1289-1296.
56. S. V Vyazovkin, A. I. Lesnikovich, Thermochim. Acta 1990, 165, 273-280.