Vilsmeier Reaction on Carbazole: Theoretical and Experimental Aspects

Abstract

The pathway of the Vilsmeier reaction on carbazole has been studied by AM1 semiempirical MO calculations, which includes the characterization of the various transition structures; an experimental study of the actual reaction shows the formation of diformyl derivative along with a monoformyl derivative.

References

1. D. P. Chakraborty, in The Alkaloids, ed. G. A. Cordell, Academic Press, New York, 1993, vol. 44, p. 257.
2. N. P. Buu-Hoi and N. Hoán, J. Am. Chem. Soc., 1951, 73, 98.
3. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
4. J. J. P. Stewart, J. Comput. Aided Mol. Design, 1990, 4, 1.
5. For example, see D. Reid, R. Webster and S. Mckenzie, J. Chem. Soc., Perkin Trans. 1, 1979, 2334; C. P. Traas, H. J. Takken and H. Boelens, Tetrahedron Lett., 1977, 18, 2129; E. M. Becalli, A. Marchesini and H. Molinari, Tetrahedron Lett., 1986, 27, 627; G. F. Smith, J. Chem. Soc., 1954, 3842; T. Shono, Y. Matsumura, K. Tsubata and Y. Sugihara, Tetrahedron Lett., 1975, 16, 3391.
6. R. Livingstone, in Rodd's Chemistry of Carbon Compounds, ed. S. Coffey, Elsevier, Amsterdam, 2nd edn., 1973, vol. 4 (Part A), p. 486.