On the reaction of diphenylketene with isocyanides

Organic and Biomolecular Chemistry

Volumn 3, Issue 23, 2005, Pages 4246-4251

  Robertson, Jeremy ^a   Bell, Stephen J ^a   Krivokapic, Alexander ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION (PROCESS); REACTION KINETICS;

DIPHENYLKETENES; ISOCYANIDES; PERICYCLIC REACTIONS;

NITROGEN COMPOUNDS;

EID: 29144506874     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b512826a     Document Type: Article

References (39)

1. I. Ugi and K. Rosendahl, Chem. Ber., 1961, 94, 2233.
2. T. El Gomati, J. Firl and I. Ugi, Chem. Ber., 1977, 110, 1603.
3. E. G. Ter-Gabrielyan, E. A. Avetisyan and N. P. Gambarayan, Izv. Akad. Nauk. SSSR, Ser. Khim., 1973, 2562.
4. H. W. Moore and C.-C. Yu, J. Org. Chem., 1981, 46, 4935.
5. R. W. Hoffmann, W. Lilienblum and B. Dittrich, Chem. Ber., 1974, 107, 3395.
6. T. Mukaiyama, H. Nambu and M. Okamoto, J. Org. Chem., 1962, 27, 3651.
7. J. E. Baldwin and J. C. Swallow, J. Org. Chem., 1970, 35, 3583.
8. W. G. Bentrude, W. D. Johnson and W. A. Khan, J. Am. Chem. Soc., 1972, 94, 3058.
9. R. N. Pratt, D. P. Stokes and G. A. Taylor, J. Chem. Soc., Perkin Trans. 1, 1975, 498.
10. A. F. Gettins, N. A. Hashi, D. P. Stokes, G. A. Taylor and K. J. Wyse, J. Chem. Soc., Perkin Trans. 1, 1985, 2501.
11. Aside from the special case of oxidopyridinium ions, other nitrogen-substituted oxyallyl species have been reported and have been shown to enter into cycloaddition chemistry: (a) M. A. Walters, H. R. Arcand and D. J. Lawrie, Tetrahedron Lett., 1995, 36, 23;
12. (b) M. A. Walters and H. R. Arcand, J. Org. Chem., 1996, 61, 1478;
13. (c) H. Xiong, R. P. Hsung, C. R. Berry and C. Rameshkumar, J. Am. Chem. Soc., 2001, 123, 7174;
14. (d) C. Rameshkumar, H. Xiong, M. R. Tracey, C. R. Berry, L. J. Yao and R. P. Hsung, J. Org. Chem., 2002, 67, 1339;
15. (e) H. Xiong, R. P. Hsung, L. Shen and J. M. Hahn, Tetrahedron Lett., 2002, 43, 4449;
16. (f) H. Xiong, J. Huang, S. K. Ghosh and R. P. Hsung, J. Am. Chem. Soc., 2003, 125, 12694;
17. (g) C. Rameshkumar and R. P. Hsung, Angew. Chem., Int. Ed., 2004, 43, 615;
18. (h) J. Huang and R. P. Hsung, J. Am. Chem. Soc., 2005, 127, 50.
19. Further details may be found in S. J. Bell, D.Phil. Thesis, Oxford, 2004.
20. int = 0.0395), 5496 reflections used, final wR = 0.0460;
21. int = 0.0509), 3035 reflections used, final wR = 0.0508;
22. int = 0.0396), 5775 reflections used, final wR = 0.0415.
23. The enhanced reactivity of α-ketoimines towards ketenes has been described and the process used as a synthetically useful entry to acyl β-lactams: (a) S. B. Singh and K. N. Mehrotra, Can. J. Chem., 1982, 60, 1901;
24. (b) B. Alcaide, M. A. Léon-Santiago, R. Pérez-Ossorio, J. Plumet, M. A. Sierra and M. C. De La Torre, Synthesis, 1982, 989.
25. Cf. (a) A. G. Myers and J. K. Barbay, Org. Lett., 2001, 3, 425;
26. (b) M. Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu and P. Kirchoefer, J. Am. Chem. Soc., 2003, 125, 2058.
27. int = 0.0413), 5345 reflections used, final wR = 0.0507;
28. int = 0.0537), 7987 reflections used, final wR = 0.0430.
29. (a) Iodide 22: L. C. Baillie, A. Batsanov, J. R. Bearder and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1998, 3471;
30. (b) modified Gabriel procedure: H. Yinglin and H. Hongwen, Synthesis, 1990, 122;
31. 2 E. Allenstein and V. Beyl, Chem. Ber., 1967, 100, 3551;
32. (d) amide 23 is a known compound: G.-D. Tebben, K. Rauch, C. Stratmann, C. M. Williams and A. de Meijere, Org. Lett., 2003, 5, 483;
33. (e) for the alkylation of 2-methylfuran with 1-bromo-3-chloropropane: C. Rogers and B. A. Keay, Can. J. Chem., 1992, 70, 2929.
34. I. D. Kuntz, Jr., P. von R. Schleyer and A. Allerhand, J. Chem. Phys., 1961, 35, 1533.
35. L. I. Smith and H. H. Hoehn, Org. Synth., 1955, Coll. Vol. III, 356.
36. tert-Butylisocyanide (12) is commercially available, (a) For 11: R. E. Schuster, J. E. Scott and J. Casanova, Org. Synth., 1973, Coll. Vol. V, 772;
37. (b) for 13: H. M. Walborsky and G. E. Niznik, J. Org. Chem., 1972, 37, 187;
38. (c) for 14: T. Isobe and T. Ishikawa, J. Org. Chem., 1999, 64, 6984.
39. M. Westling, R. Smith and T. Livinghouse, J. Org. Chem., 1986, 51, 1159.