Summary
-
1.
In the infrared spectra of a number of acylmethylenetriphenylphosphoranes, the bands of the carbonyl groups are displaced in the low-frequency direction, while in the spectra of phosphonium salts, these bands occupy a normal position.
-
2.
The intensities of the carbonyl bands in the spectra of acylmethylenetriphenylphosphoranes are considerably increased, while in the spectra of the salts they are somewhat reduced in comparison with the normal values.
-
3.
The data obtained agree with the ylide structure of acylmethylenetriphenylphosphoranes, in which the polarity of the C=O groups is greatly increased, and the negative charge is localized to a considerable degree on the oxygen, rather than on the ylide carbon as in alkylidenephosphoranes.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
G. Wittig and U. Schollkopf, Chem. Ber.,87, 1318 (1954).
R. Ramirez and S. Dershowitz, J. Organ. Chem.,22, 41 (1957).
G. Aksnes, Acta Chem. Scand.,15, 692 (1961).
L. Brown, Chem. Rev.,58, 581 (1958).
H. W. Thompson and D. A. Jonson, Spectrochim. Acta,13, 236 (1958).
F. Ramirez and N. McKelvie, J. Am. Chem. Soc.,79, 5829 (1957).
E. B. Wilson and A. I. Wells, J. Chem. Phys.,14, 578 (1946).
D. A. Ramsay, J. Am. Chem. Soc.,74, 72 (1952).
W. West, Application of Spectroscopy in Chemistry [Russian translation] (IL, Moscow, 1959), p. 440.
L. D. Bergel'son, É. V. Dyatlovitskaya, and M. M. Shemyakin, Izv. AN SSSR, Otd. khim. n.,1963, 506.
O. Isler, H. Gutmann, M. Montavon, R. Rüegg, G. Reyser, and P. Zeller, Helv. Chim. Acta,40, 1242 (1957).
A. Michaelis and E. Kohler, Ber.,32, 1566 (1899).
L. D. Bergel'son, V. A. Vaver, L. I. Barsukov, and M. M. Shemyakin, Izv. AN SSSR, Otd. khim. n.,1963, 1135.
E. Buchta and F. Andrée, Chem. Ber.,92, 3111 (1959).
S. Trippett and D. M. Walker, J. Chem. Soc.,1961, 1266.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 11, pp. 1979–1984, November, 1964
Rights and permissions
About this article
Cite this article
Senyavina, L.V., Dyatlovitskaya, É.V., Sheinker, Y.N. et al. Infrared spectra of acylmethylenetriphenylphosphoranes and their salts. Russ Chem Bull 13, 1884–1888 (1964). https://doi.org/10.1007/BF00844481
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00844481