Abstract
The Wittig reaction with indole-3-aldehyde and its N-acetyl derivative has been studied. Data are presented on the influence of various factors on the formation of the unsaturated compound. Some hypotheses are put forward concerning the reactivity of indole-3-aldehydes under the conditions of this reaction. The previously unknown α-(indol-3-yl)-β-phenylethylene has been obtained with a yield of 54%.
Similar content being viewed by others
References
H. H. Inhoffen, K. Brückner, G. F. Domagk, and H. M. Erdmann, Ber.,88, 1415, 1955.
F. Bohlman, Ber., 90, 1519, 1957.
G. Witschard and C. E. Griffen, J. Org. Chem.,29, 2335, 1964.
L. N. Yakhontov, L. I. Mastafanova, and M. V. Rubtsov, ZhOKh,33, 3211, 1963.
J. R. Alan and J. A. Lindner, Austral. J. Chem.,18, 875, 1965.
T. Gramstad and W. J. Fuglevik, Spectrochim. Acta,21, 503, 1965.
U. Schölkopf, Angew. Chem.,71, 264, 1959.
L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], Moscow, 1963.
J. M. Daly and B. Witkop, J. Org. Chem.,27, 4105, 1962.
NMR Spectra Catalog, Var. No. 231, 594, 305, 306, 1963.
P. Isler, Helv. Chim. Acta,40, 1242, 1957.
G. Wittig and W. Haag, Ber.,88, 1654, 1955.
L. Horner and A. Mentrup, Ann.,646, 65, 1961.
H. O. House, V. K. Jones, and G. A. Frank, J. Org. Chem.,29, 3327, 1964.
Yu. I. Smushkevich, Ts. M. Babueva, and N. N. Suvorov, KhGS [Chemistry of Heterocyclic Compounds],5, 91, 1969.
Author information
Authors and Affiliations
Additional information
For part XXXIV, see [15].
Rights and permissions
About this article
Cite this article
Suvorov, N.N., Orlova, I.A. & Turchin, K.F. Indole derivatives. Chem Heterocycl Compd 5, 190–193 (1969). https://doi.org/10.1007/BF00943911
Issue Date:
DOI: https://doi.org/10.1007/BF00943911