Reactions of thioamides with metal carboxylates in organic media

Tetrahedron

Volumn 53, Issue 42, 1997, Pages 14463-14480

  Avalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Durán, Carlos J ^a   Higes, Francisco J ^a   Jiménez, José L ^a   López, Ignacio ^a   Palacios, Juan C ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; IMIDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030865140     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00938-1     Document Type: Article

References (55)

1. a) Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds; Barton, D.; Ollis, W. D.; Jones, D. N., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, Part 11, pp 3-487.
2. b) Schaumann, E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Winterfeldt, E., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 419-434.
3. Satchell, D. P. N.; Satchell, R. S. in The Chemistry of Sulphur-Containing Functional Groups; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1993; Supplement S, Chapter 12, pp 599-631.
4. Avalos, M.; Babiano, R.; Cintas, P.; Durán, C. J.; Jiménez, J. L.; Palacios, J. C. Tetrahedron 1995, 51, 8043-8056.
5. a) Foloppe, M. P.; Rault, S.; Robba, M. Tetrahedron Lett. 1992, 33, 2803-2804.
6. b) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
7. Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461-7462.
8. Levallet, C.; Lerpiniere, J.; Ko, S. Y. Tetrahedron 1997, 53, 5291-5304.
9. Hurd, R. N.; DeLaMater, G. Chem. Rev. 1961, 61, 45-86.
10. Walter, W.; Voss, J. in The Chemistry of Amides; Zabicky, J., Ed.; Wiley-Interscience: New York, 1970; pp 383-475.
11. a) For a review on silver carboxylates and other silver salts: Long, J. R. Aldrichimica Acta 1981, 14, 63-70.
12. b) Mehrotra, R. C.; Bohra, R. Metal Carboxylates; Academic Press: London, 1983.
13. Oldham, C. in Comprehensive Coordination Chemistry; Wilkinson, G.; Guillard, R. D.; McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 435-459.
14. For transition metal carboxylates as acylating agents: Recht, J.; Cohen, B. I.; Goldman, A. S.; Kohn, J. Tetrahedron Lett. 1990, 31, 7281-7284.
15. e) See also: Joshi, K.; Bao, J.; Goldman, A. S.; Kohn, J. J. Am. Chem. Soc. 1992, 114, 6649-6652.
16. f) For a review on the coordination chemistry of cyclopentadienyl titanium carboxylates and related complexes: Dang, Y. Coord. Chem. Rev. 1994, 135/136, 93-128.
17. Marchand-Brynaert, J.; Moya-Portuguez, M.; Huber, I.; Ghosez, L. J. Chem. Soc., Chem. Commun. 1983, 818-819.
18. Taylor, E. C.; McKillop, A. in Advances in Organic Chemistry. Methods and Results; Taylor, E. C., Ed.; Wiley-Interscience: New York, 1970; Vol. 7, p 180.
19. a) Kjaer, A. Acta Chem. Scand. 1952, 6, 1374-1383.
20. b) El Khadem, H. S.; Kawai, J.; Swartz, D. L. Carbohydr. Res. 1989, 189, 149-160.
21. M. Avalos, Babiano, R.; Durán, C. J.; Jiménez, J. L.; Palacios, J. C. Tetrahedron Lett. 1994, 35, 477-480.
22. Lim, M.-I.; Ren, W.-Y.; Klein, R. S. J. Org. Chem. 1982, 47, 4594-4595.
23. Challis, B. C.; Challis, A. C. in Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds; Barton, D.; Ollis, W. D.; Sutherland, I. O., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 957-1065.
24. For recent examples: a) Radha, R. B.; Rahman, M. F.; Bhalerao, U. T. Tetrahedron 1992, 48, 1953-1958.
25. b) Crestini, C.; Saladino, R.; Bernini, R.; Mincione, E. Tetrahedron Lett. 1993, 34, 7785-7788.
26. Creary, X.; Zhu, C. J. Am. Chem. Soc. 1995, 117, 5859-5860.
27. Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419-4438.
28. Frère, P.; Belyasmine, A.; Gorgues, A.; Duguay, G.; Boubekeur, K.; Batail, P. Tetrahedron Lett. 1993, 34, 4519-4522.
29. a) Burman, S.; Sathyanarayana, D. N. J. Inorg. Nucl. Chem. 1981, 43, 1940-1942.
30. b) Brunner, H.; Bügler, J.; Nuber, B. Tetrahedron: Asymmetry 1996, 7, 3095-3098.
31. The authors have deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
32. a) For complexes of heterocyclic thione donors: Raper, E. S. Coord. Chem. Rev. 1985, 61, 115-184.
33. b) Vagg, R. S. in Comprehensive Coordination Chemistry; Wilkinson, G.; Guillard, R. D.; McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, pp 793-812.
34. a) Canty, A. J.; Deacon, G. B. Inorg. Chim. Acta 1980, 45, L225-L227.
35. b) Atwood, J. L.; Berry, D. E.; Stobart, S. R.; Zaworotko, M. J. Inorg. Chem. 1983, 22, 3480-3482.
36. a) Kiefer, E. F.; Waters, W. L.; Carlson, D. A. J. Am. Chem. Soc. 1968, 90, 5127-5131.
37. b) Bach, R. D.; Weibel, A. T.; Schmosees, W.; Glick, M. D. J. Chem. Soc., Chem. Commun. 1974, 961-962.
38. Alcock, N. W.; Lampe, P. A.; Moore, P. J. Chem. Soc., Dalton Trans. 1978, 1324-1328.
39. a) For a review on the Chapman rearrangement: Schulenberg, J. W.; Archer, S. Org. React. 1965, 14, 1-51 and references cited therein.
40. b) For the mechanism of the isoimide-imide rearrangement: Brady, K.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1980, 121-126.
41. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
42. Vogel's Textbook of Practical Organic Chemistry, 5th Ed.; Longman Scientific & Technical and John Wiley & Sons: New York, 1991; pp 220-221.
43. Dictionary of Organic Compounds; Pollock, J. R. A.; Stevens, R., Eds.; Eyre-Spottiswoode Publishers: London, 1965; Vol. 1, p 346.
44. Ref. 25, Vol. 2, p 768.
45. Ref. 25, Vol. 2, p 768.
46. Ref. 25, Vol. 2, p 845.
47. Avalos, M.; Babiano, R.; Durán, C. J.; Jiménez, J. L.; Palacios, J. C. J. Chem. Soc., Perkin Trans. 2 1992, 2205-2215.
48. Inch, T. D.; Fletcher, Jr., H. G. J. Org. Chem. 1966, 31, 1815-1820.
49. Edmundson, M. J. Chem. Soc., C 1971, 3437-3440.
50. Ref. 25, Vol. 1, p 8.
51. Lewin, A. H.; Frucht, M.; Chen, K. V. J.; Benedetti, E.; Di Blasio, B. Tetrahedron 1975, 31, 207-215.
52. Gómez, M.; Galbis, J. A.; Areces, P.; Fernández, J. I.; Avalos, M.; Ramírez, J. M. An. Quim. 1978, 74, 633-636.
53. Williams, A. J. Am. Chem. Soc. 1976, 98, 5645-5651.
54. Johnson, J. R.; McEwen, W. L. J. Am. Chem. Soc. 1926, 48, 469-476.
55. The boiling point was determined by comparison with an authentical sample from Aldrich Chemical Co.