Dehydration of formamides using the Burgess Reagent: a new route to isocyanides

Abstract

The Burgess Reagent readily converts formamides into isocyanides in high yields and is particularly effective for substrates containing halide sensitive trimethylsilyl ether groups.

References

1. D. P. Curran, S. B. Ko and H. Josien, Angew. Chem., Int. Ed. Engl., 1995, 34, 2683; M. Bachi and A. Melman, Synlett, 1996, 60; M. Bachi and M. Melman, J. Org. Chem., 1997, 62, 1896; T. Kercher and T. Livinghouse, J. Org. Chem., 1997, 62, 805; M. Yamada, T. Fukui and K. Nunami, Synthesis, 1995, 1365; M. Suginome, H. Nakamura and Y. Ito, Tetrahedron Lett., 1997, 38, 555.
2. R. J. Sundberg, Progress in Heterocyclic Chemistry, eds. H. Suschitzky and G. W. Gribble, Pergamon, Oxford, 1996, vol. 8, p. 104; T. Q. Dinh and R. W. Armstrong, J. Org. Chem., 1995, 60, 8118; A. M. Strocker, T. A. Keating, P. A. Tempest and R. W. Armstrong, Tetrahedron Lett., 1996, 37, 1149.
3. I. A. O'Neil, Comprehensive Organic Functional Transformations, ed. G. Pattenden(Series eds. A. R. Katritzky, O. Meth-Cohn and C. W. Rees), Elsevier, Oxford, 1995, vol. 3, p. 693.
4. G. M. Atkins, Jr. and E. M. Burgess, J. Am. Chem. Soc., 1968, 90, 4744; A. Hassner and C. Stumer, Organic Synthesis Based On Name Reactions and Unnamed Reactions, Pergamon, Oxford, 1994, p. 56.
5. M. I. Casey, H. K. Crowley and D. G. McCarthy, unpublished results.
6. G. Giesmann, E. von Hinrichs and I. Ugi, J. Chem. Res. (S), 1982, 79; S. Kim and K. Yang Yi, Tetrahedron Lett., 1986, 27, 1925; J. E. Baldwin and I. A. O'Neil, Synlett, 1990, 603.
7. (a) E. M. Burgess, H. R. Penton, Jr. and E. A. Taylor, J. Org. Chem., 1973, 38, 26; (b) P. Crabbe and C. Leon, J. Org. Chem., 1970, 35, 2594; (c) J. S. O'Grodnick, R. C. Ebersole, T. Wittstruck and E. Caspi, J. Org. Chem., 1974, 39, 2124; (d) R. McCague, J. Chem. Soc., Perkin Trans. 1, 1987, 1011; (e) S. M. Rubenstein and R. M. Williams, J. Org. Chem., 1995, 60, 7215.
8. (a) P. Wipf and C. P. Miller, Tetrahedron Lett., 1992, 33, 907; (b) P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604; (c) E. Aguilar and A. I. Meyers, Tetrahedron Lett., 1994, 35, 2477; (d) P. Wipf and P. C. Fritch, Tetrahedron Lett., 1994, 35, 5397; (e) R. J. Boyce, G. C. Mulqueen and G. Pattenden, Tetrahedron Lett., 1994, 35, 5705; (f) P. Wipf and W. Xu, J. Org. Chem., 1996, 61, 6556; (g) P. Wipf and S. Venkatraman, Tetrahedron Lett., 1996, 37, 4659.
9. D. A. Claremon and B. T. Phillips, Tetrahedron Lett., 1988, 29, 2155; N. Maugein, A. Wagner and C. Mioskowski, Tetrahedron Lett., 1997, 38, 1547.
10. D. F. Morrow, M. E. Butler and E. C. Y. Huang, J. Org. Chem., 1965, 28, 579.
11. D. H. R. Barton, G. Bringmann, G. Lamotte, W. B. Motherwell, R. S. Hay-Motherwell and A. E. Porter, J. Chem. Soc., Perkin Trans. 1, 1980, 2657.
12. S. Czernecki and J.-M. Valery, J. Chem. Soc., Chem. Commun., 1990, 801; J. P. H. Verheyen and J. G. Moffatt, J. Org. Chem., 1974, 39, 3573.