Nucleophilic carbenes and the Wanzlick equilibrium: A reinvestigation

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2057-2060

  Denk, Michael K ^a   Hatano, Ken ^a   Ma, Martin ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033548525     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00164-1     Document Type: Article

References (45)

1. a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494; Wanzlick, H.-W.; Schikora, E. Chem. Ber. 1961, 94, 2389-2393;
2. a) Wanzlick, H.-W.; Schikora, E. Angew. Chem. 1960, 72, 494; Wanzlick, H.-W.; Schikora, E. Chem. Ber. 1961, 94, 2389-2393;
3. b) Wanzlick, H.-W.; Kleiner, H.-J. Angew. Chem. 1961, 73, 493;
4. c) Wanzlick, H.-W. Angew. Chem. 1962, 74, 129-134; Wanzlick, H.-W. Angew. Chem. Int. Ed. Engl. 1962, I, 75-80;
5. c) Wanzlick, H.-W. Angew. Chem. 1962, 74, 129-134; Wanzlick, H.-W. Angew. Chem. Int. Ed. Engl. 1962, I, 75-80;
6. e) Wanzlick H.-W.; Ahrens, H. Chem. Ber. 1964, 97, 2447-2445;
7. f) Wanzlick, H.-W.; Lachmann, B.; Schikora, E. ibid 1965, 98, 3170-3177;
8. g) Wanzlick, H.-W.; Schönherr, H. J. Angew. Chem. 1968, 80, 153-154; Angew. Chem. Int. Ed Engl. 1968, 7, 141-142.
9. g) Wanzlick, H.-W.; Schönherr, H. J. Angew. Chem. 1968, 80, 153-154; Angew. Chem. Int. Ed Engl. 1968, 7, 141-142.
10. Wiberg, N. Angew. Chem. 1968, 80, 809-833; Angew. Chem. Int. Ed Engl. 1968, 7, 766-779.
11. Wiberg, N. Angew. Chem. 1968, 80, 809-833; Angew. Chem. Int. Ed Engl. 1968, 7, 766-779.
12. Quast, H.; Hünig, S. Chem. Ber. 1966, 99, 2017-2038.
13. a) Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1967, 7, 754-765; Angew. Chem. 1968, 80, 823;
14. a) Hoffmann, R. W. Angew. Chem. Int. Ed. Engl. 1967, 7, 754-765; Angew. Chem. 1968, 80, 823;
15. b) Lemal, D. M. in The Chemistry of The Amino Group (Ed.: S. Patai), John Wiley & Sons, London, 1968, p. 701-748;
16. c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem. Int. Ed. Engl. 1972, 11, 964-973;
17. c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem. Int. Ed. Engl. 1972, 11, 964-973;
18. d) Regitz, M. Methoden Org. Chem. (Houben-Weyl), 4th Ed. 1952-, Vol. E19b, Thieme, Stuttgart, 1989;
19. e) Haug, E.; Kantlehner, W. in: Methoden Org. Chem. (Houben-Weyl), 4th Ed. 1952-, Vol E15, 2898-2904, Thieme, Stuttgart, 1993.
20. a) Hitchcock, P. B.; Lappert, M. F.; Pye, P. L. J. Chem. Soc., Chem. Commun. 1977, 196-198;
21. b) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214;
22. c) Çetinkaya, E.; Hitchcock, P. B.; Jasim, H. A.; Lappert, M. F.; Spyropoulos, K. J. Chem. Soc. Perkin Trans, I 1992, 561-567;
23. d) Çetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Shaw, D. B.; Spyropoulos, K.; Warhurst, N. J. W. J. Organomet. Chem. 1993, 459, 311-317.
24. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Eng. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721; see also: Alder, R. W.; Blake, M. E. Chem. Commun. 1997, 1513-1514.
25. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Eng. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721; see also: Alder, R. W.; Blake, M. E. Chem. Commun. 1997, 1513-1514.
26. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Eng. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721; see also: Alder, R. W.; Blake, M. E. Chem. Commun. 1997, 1513-1514.
27. a) Denk, M.; Lennon, R.; Hayashi, R.; West, R.; Belyakov, A. V.; Verne, H. P.; Haaland, A.; Wagner, M.; Metzler, N. J. Am. Chem. Soc. 1994, 116, 2691-2692;
28. b) Denk, M.; Hayashi, R. K.; West, R. J. Chem. Soc., Chem. Commun. 1994, 33-34;
29. c) Denk, M.; Green, J.; Metzler, N.; Wagner, M. J. Chem. Soc., Dalton Trans. 1994, 2405-2410;
30. d) Metzler, N.; Denk, M. J. Chem. Soc., Chem. Commun. 1996, 2657-2658;
31. e) Urquhart, S.; Hitchcock, A. P.; Denk, M. K. Organometallics 1998, 17, 2352- 2360;
32. f) Denk, M. K.; Hatano, K.; Lough, A. J. Eur. J. Inorg. Chem. 1998, 1067-1070.
33. Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F.-R.; Bock, H.; Solouki, B.; Wagner, M. Angew. Chem. 1992, 104, 1489-1492; Angew. Chem. Int. Ed. Engl. 1992, 31, 1485-1488.
34. Herrmann, W. A.; Denk, M.; Behm, J.; Scherer, W.; Klingan, F.-R.; Bock, H.; Solouki, B.; Wagner, M. Angew. Chem. 1992, 104, 1489-1492; Angew. Chem. Int. Ed. Engl. 1992, 31, 1485-1488.
35. a) Denk, M. K.; Gupta, S.; Ramachandran, R. Tetrahedron Lett. 1996, 37, 9025-9028;
36. b) Denk, M. K.; Gupta, S.; Lough, A. J. Eur. J. Inorg. Chem. 1999, 41-49.
37. The corresponding CC-unsaturated carbenes do not dimerize even in the absence of sterically demanding substituents: a) Shi, Z.; Goulle, V.; Thummel, R. G. Tetrahedron Lett. 1996, 37, 2357- 2360;
38. b) Tormos, G. V.; Bakker, M. G.; Wang, P.; Lakshmikantham, M. V.; Cava, M. P.; Metzger, R. M. J. Am. Chem. Soc. 1995, 117, 8528-8535;
39. c) Taton, T. A.; Chen, P. Angew. Chem. 1996, 108, 1098-1100; Angew. Chem. Int. Ed. Engl. 1996, 35, 1011-1013.
40. c) Taton, T. A.; Chen, P. Angew. Chem. 1996, 108, 1098-1100; Angew. Chem. Int. Ed. Engl. 1996, 35, 1011-1013.
41. Lemal, D. M.; Lovald, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518-2519.
42. Winberg, H. E.; Carnahan, J. E.; Coffman, D. D.; Brown, M. J. Am. Chem. Soc. 1965, 87, 2055-2056.
43. This is likely due to the low solubility of 1d in benzene( 1d < 3d < 1e < 1a-c).
44. The thermal dimerization of two electron rich olefins is highly unlikely in our opinion, and a similar argument based on the relative electron demand applies to the reaction of an enetetramine with a nucleophilic carbene.
45. Results presented at The 1998 Canadian Society for Chemistry Conference, May 31 - June 4. 1998, Whistler, BC.