A stable thiazol-2-ylidene and its dimer

Liebigs Annales

Volumn , Issue 2, 1997, Pages 365-374

  Arduengo III, Anthony J ^a   Goerlich, Jens R ^a   Marshall, William J ^a  

^a Applied Science and Engineering Laboratories   (United States)

Author keywords

Carbene dimer; Carbenes; Dimerizations; Thiazol 2 ylidene; Ylides

Indexed keywords

EID: 33748842769     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970213     Document Type: Article

References (59)

1. A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.
2. A. J. Arduengo III, H. V. R. Dias, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1992, 114, 5530.
3. A. J. Arduengo III, J. R. Goerlich, W. J. Marshall, J. Am. Chem. Soc. 1995, 117, 11027.
4. D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
5. R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211.
6. R. Kluger, Chem. Rev. 1987, 87, 863.
7. H.-W. Wanzlick, H.-J. Kleiner, Angew. Chem., Int. Ed Engl. 1964, 5, 65.
8. H. Quast, S. Hünig, Angew. Chem., Int. Ed. Engl. 1964, 3, 800.
9. J.-J. Vorsanger, Bull. Soc. Chim. France 1964, 119.
10. H. Susimoto, K. Hirai, Tetrahedron Lett. 1985, 26, 883.
11. H. Susimoto, K. Hirai, Heterocycles 1987, 26, 13.
12. H. Susimoto, K. Hirai, Heterocycles 1988, 27, 877.
13. H. Susimoto, T. Ishiba, T. Sato, H. Nakai, K. Hirai, J. Org. Chem. 1990, 55, 467.
14. R. Breslow, Chem. Ind. 1957, 893.
15. R. Breslow, Ann. N. Y. Acad Sci. 1962, 98, 445.
16. H. Quast, S. Hünig, Chem. Ber. 1966, 99, 2017.
17. M. W. Washabauch, W. P. Jencks, Biochemistry 1988, 27, 5044.
18. F. G. Bordwell, A. V. Satish, J. Am. Chem. Soc. 1991, 113, 985.
19. Y.T. Chen, F. Jordan, J. Org. Chem. 1991, 56, 5029.
20. G. V. Tormos, M. G. Bakker, P. Wang, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger, J. Am. Chem. Soc. 1995, 117, 8528.
21. J. H. Teles, J.-P. Melden K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Brode, D. Enders, K. Breuer, G. Raabe, Helv. Chim. Acta 1996, 79, 61.
22. D. A. Dixon, A. J. Arduengo III, J. Phys. Chem. 1991, 95, 4180.
23. J. Cioslowski, Int. J. Quant. Chem.: Quant. Chem. Sympos. 27, 1993, 27, 309.
24. C. Heinemann, W. Thiel, Chem. Phys. Lett. 1994, 217, 11.
25. A. J. Arduengo III, H. V. R. Dias, D. A. Dixon, R. L. Harlow, W. T. Klooster, T. F. Koetzle, J. Am. Chem. Soc. 1994, 116, 6812.
26. A. J. Arduengo III, D. A. Dixon, K. K. Kumashiro, C Lee, W. P. Power, K. W. Zilm, J. Am. Chem. Soc. 1994, 116, 6361.
27. A. J. Arduengo III, H. Bock, H. Chen, D. A. Dixon, J. C. Green, W. A. Herrmann, N. L. Jones, M. Wagner, R. West, J. Am. Chem. Soc. 1994, 116, 6641.
28. G. Raabe, K. Breuer, D. Enders, J. H. Teles, Z. Naturforsch. 1996, 51a, 95.
29. A. E. Heinemann, T. Müller, Y. Apeloig, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 2023.
30. C. Boehme, G. Frenking, J. Am. Chem. Soc. 1996, 118, 2039.
31. J. Liebscher, Methoden der Organischen Chemie (Houben-Weyl), 4th ed. (Ed.: E. Schaumann), Georg Thieme Verlag, New York, 1994, Band E 8b, Hetarene III/Part 2, p. 48.
32. O. Hromatka, U.S. Patent 2160867, 1939.
33. This drawing was made with the KANVAS computer graphics program. This program is based on the program SCHAKAL of E. Keller (Kristallographisches Institut der Universität Freiburg, Germany), which was modified by A. J. Arduengo, III (E. I. du Pont de Nemours and Co., Wilimington, DE) to produce the back and shadowed planes. The planes bear a 50-pm grid and the lighting source is at infinity so that shadow size is meaningful.
34. A. J. Arduengo III, H. V. R. Dias, J. C. Calabrese, F. Davidson, Inorg. Chem. 1993, 32, 1541.
35. T. Takabe, H. Fukutome, Prog. Theor. Phvs. 1976, 56, 689.
36. H. Fujimoto, S. Yamabe, K. Fukui, Bull. Chem. Soc. Jpn. 1972, 45, 1566.
37. R. Sustmann, G. Binsch, Mol. Phys. 1971, 20, 1.
38. H. Kollmar, Tetrahedron Lett. 1970, 38, 3337.
39. R. Hoffmann, R. Gleiter, F. B. Mallory, J. Am. Chem. Soc. 1970, 92, 1460.
40. G. C. Levy, R. L. Lichter, "Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy", Wiley: New York, 1979; p. 77.
41. P. Diehl, E. Fluck, R. Kosfeld, in Nuclear Magnetic Resonance; Springer-Verlag: New York, 1981; p. 127.
42. The N-X-L nomenclature system has been previously described (C. W. Perkins, J. C. Martin, A. J. Arduengo, III, W. Lau, A. Algeria, J. K. Kochi, J. Am. Chem. Soc. 1980, 102, 7753). N valence electrons about a central atom X, with L ligands.
43. 2, which suggests that nitrogen inversion barriers are low or nonexistent.
44. M. Regitz, Angew. Chem. Int. Ed. Engl. 1991, 30, 674.
45. 13C spectra reported by Hirai et al. that should be reexamined.
46. G. Boche, P. Andrews, K. Harms, K. Marsch, K. S. Rancappa, M. Schimeczek, C. Willeke, J. Am. Chem. Soc. 1996, 118, 4925.
47. P. G. Jones, O. Kennard, Acta Crystallogr. 1978, B34, 335.
48. G. Boche, C. Hilf, K. Harms, M. Marsch, J. C. W. Lohrenz, Angew. Chem., Int. Ed. Engl. 1995, 34, 487.
49. [50,51,54].
50. A. Igau, H. Grützmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463.
51. D. A. Dixon, K. D. Dobbs, A. J. Arduengo III, G. Bertrand, J. Am. Chem. Soc. 1991, 113, 8782.
52. N. Kuhn, T. Kratz, Synthesis 1993, 561.
53. [54].
54. B. Pötter, K. Seppelt, A. Simon, E.-M. Peters, B. Hettich, J. Am. Chem. Soc. 1985, 107, 980.
55. A. J. Arduengo, R. Herges, unpublished results.
56. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals; Pergamon: New York, 1985.
57. 6 in glass vials led to spontaneous dimerization within days, although the presence of KH inhibits this reaction.
58. 6 showed broad unresolved signals, only when KH was present in the mixture sharp signals were obtained.
59. 2, including tables of fractional coordinates, isotropic and anisotropic thermal parameters, bond lengths, bond angles and ORTEP drawings, has been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge GB2 1EZ, UK, depository number CCDC-100053.