Blue, but not a mirage: Stable aminoketenes by carbene carbonylation

Angewandte Chemie - International Edition

Volumn 45, Issue 34, 2006, Pages 5580-5582

  Tidwell, Thomas T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Carbenes; Carbonylation; Intermediates; Ketenes; Reactive; Synthetic methods

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBENES; HOMO-LUMO INTERACTIONS; SYNTHETIC METHODS;

OLEFINS;

EID: 33748558819     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601643     Document Type: Short Survey

References (36)

1. a) H. Staudinger, Ber. Dtsch. Chem. Ges. 1905, 38, 1735-1739;
2. b) for a historical account of the development of ketene chemistry, see: T. T. Tidwell, Angew. Chem. 2005, 117, 5926-5933;
3. Angew. Chem. Int. Ed. 2005, 44, 5778-5785;
4. c) for a review of recent developments in ketene chemistry, see: T. T. Tidwell, Eur. J. Org. Chem. 2006, 563-576;
5. d) T. T. Tidwell, Ketenes, 2nd ed., Wiley, Hoboken, 2006.
6. a) H. Staudinger, O. Kupfer, Ber. Dtsch. Chem. Ges. 1911, 44, 1638-1640;
7. b) H. Staudinger, H. Schneider, Helv. Chim. Acta 1923, 6, 304-315;
8. c) G. Maier, C. Rohr, Liebigs Ann. 1996, 307-309;
9. d) A. V. Fedorov, E. O. Danilov, A. G. Merzlikine, M. A. J. Rogers, D. C. Neckers, J. Phys. Chem. A 2003, 107, 3208-3214;
10. e) T. Sugimura, Eur. J. Org. Chem. 2004, 1185-1192.
11. a) H. Staudinger, E. Anthes, H. Schneider, Ber. Dtsch. Chem. Ges. 1913, 46, 3539-3541;
12. b) E. Ott, Justus Liebigs Ann. 1913, 401, 159-177;
13. c) H. C. Stevens, D. A. Reich, D. R. Brandt, K. R. Fountain, E. J. Gaughan, J. Am. Chem. Soc. 1965, 87, 5257-5259;
14. d) W. T. Brady, H. G. Liddell, W. L. Vaughn, J. Org. Chem. 1966, 31, 626-628;
15. e) L. Ghosez, R. Montaigne, P. Mollet, Tetrahedron Lett. 1966, 135-139.
16. a) J. C. Sheehan, E. L. Buhle, E. J. Corey, G. D. Laubach, J. J. Ryan, J. Am. Chem. Soc. 1950, 72, 3829-3830;
17. b) J. C. Sheehan, E. J. Corey, J. Am. Chem. Soc. 1951, 73, 4756-4759;
18. c) J. C. Sheehan, The Enchanted Ring, MIT Press, Cambridge, 1982.
19. a) J. C. Sheehan, J. J. Ryan, J. Am. Chem. Soc. 1951, 73, 1204-1206;
20. J. C. Sheehan, J. J. Ryan, J. Am. Chem. Soc. 1951, 73, 4367-4372;
21. b) J. C. Sheehan, E. J. Corey, Org. React. 1957, 9, 388-408;
22. c) C. Palomo, J. M. Aizpurua, Science of Synthesis (Houben-Weyl), Vol. 23.6 (Eds.: D. Bellus, R. Danheiser), Thieme, Stuttgart, 2006;
23. d) W. Reichen, Chem. Rev. 1978, 78, 569-588.
24. S. Winter, H. Pracejus, Chem. Ber. 1966, 99, 151-159.
25. a) L. Gong, M. A. McAllister, T. T. Tidwell, J. Am. Chem. Soc. 1991, 113, 6021-6028;
26. b) M. A. McAllister, T. T. Tidwell, J. Org. Chem. 1994, 59, 4506-4515.
27. a) S. N. Lyashchuk, Y. G. Skrypnik, Tetrahedron Lett. 1994, 35, 5271-5274;
28. b) D. A. Dixon, A. J. Arduengo III, K. D. Dobbs, D. V. Khasnis, Tetrahedron Lett. 1995, 36, 645-648.
29. a) V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Angew. Chem. 2006, 118, 3568-3571;
30. Angew. Chem. Int. Ed. 2006, 45, 3488-3491;
31. b) V. Lavallo, J. Mafhouz, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, J. Am. Chem. Soc. 2004, 126, 8670-8671;
32. c) V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851-5855;
33. Angew. Chem. Int. Ed. 2005, 44, 5705-5709.
34. a) H. Staudinger, R. Endle, Ber. Dtsch. Chem. Ges. 1913, 46, 1437-1442;
35. b) K. Knox, R. G. W. Norrish, G. Porter, J. Chem. Soc. 1952, 1477-1486;
36. c) W. F. Ross, G. B. Kistiakowsky, J. Am. Chem. Soc. 1934, 56, 1112-1115.