Summary
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1.
The reaction of ethoxyacetylene with various unsaturated aldehydes and ketones in presence of boron trifluoride ether provides a simple and convenient method for the synthesis of esters of α, β-unsaturated acids.
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2.
This method was used for the preparation of esters of important polyenic isoprenoid acids: β-ionolideneacetic and β-ionolidenecrotonic acids, and also the acid of vitamin A.
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Literature cited
H. Vieregge, H. J. T. Bos, J. F. Arens, Recueil trav. chim.78, 664 (1959).
H. J. Boonstra, J. F. Arens, Recueil trav. chim.79, 866 (1960).
Dictionary of Organic Compounds [Russian translation], IL, M., 1949, p. 632.
R. Kuhn, M. Hoffer, Ber.65, 651 (1932).
E. E. Royals, J. Amer. Chem. Soc.69, 843 (1947).
A. Caliezi, H. Schinz, Helv. chim. acta35, 1637 (1952).
A. Caliezi, H. Schinz, Helv. chim. acta33, 1129 (1950).
H. O. Huisman, A. Smit, R. Hvan Leewen, J. H. van Rij, Recueil trav. chim.75, 977 (1956).
D. A. van Dorp, I. F. Arens, Recueil trav. chim.65, 338 (1946).
B. C. D. Robeson, J. D. Cawley, L. Weisler et al., J. Amer. Chem. Soc.77, 4111 (1955).
O. Schwarzkopf, H. J. Cahnmann et al., Helv. chim. acta32, 443 (1949).