Conclusions
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1.
Trimethyl phosphite reacts with dibenzalacetone to give 2, 2, 2-trimethoxy-3-phenyl-5-(β-phenyl)-vinyl-1,2-oxa-4-phospholene (II).
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2.
The phosphorane ring is opened at the P-O bond when (II) is hydrolyzed with water, with the formation of two keto phosphonates, probably the S-cis and S-trans conformers.
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3.
Phosphorane (II) reacts with dibenzalacetone by the diene synthesis scheme.
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B. A. Arbuzov, V. M. Zoroastrova, G. A. Tudrii, and A. V. Fuzhenkova, Izv. Akad. Nauk SSSR, Ser. Khim.,1972, 2545.
F. Ramirez, O. P. Madan, and S. R. Heller, J. Am. Chem. Soc.,87, 731 (1965).
K. Noack and R. N. Jones, Can. J. Chem.,39, 2201, 2225 (1961).
E. V. Sobolev and V. T. Aleksanyan, Izv. Akad. Nauk SSSR, Ser. Khim.,1963, 1336.
K. Nakanishi, Infrared Absorption Spectroscopy [Russian translation], “Mir” (1965), p. 11.
L. J. Bellamy, New Data on Infrared Spectra of Complex Molecules [Russian translation], “Mir” (1971), p. 172.
R. L. Erskine and E. S. Waight, J. Chem. Soc.,1960, 3425.
L. J. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL (1963), p. 68.
B. A. Arbuzov, Study of Isomeric Transformations of Bicyclic Terpene Hydrocarbons and Their Oxides [in Russian], Kazan (1936), p. 44.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2581–2585, November, 1973.
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Arbuzov, B.A., Zoroastrova, V.M., Tudrii, G.A. et al. Reaction of dibenzalacetone with trimethyl phosphite and dimethylphosphorous acid. Russ Chem Bull 22, 2513–2516 (1973). https://doi.org/10.1007/BF00926407
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DOI: https://doi.org/10.1007/BF00926407