Conclusions
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1.
Heating Z-triphenyl(2-alkoxyprop-1-enyl)phosphonium iodides with diethylamine and triethylamine leads to their partial geometric isomerization.
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2.
Heating of these salts with alcohols leads to their exchange of the alkoxy group and partially reversible addition of the alcohol at the double bond in addition to isomerization.
Literature cited
N. A. Nesmeyanov, V. G. Kharitonov, S. T. Zhuzhlikova, et al., Zh. Org. Khim.,23, 1577 (1987).
H. J. Bestmann, K. Roth, and M. Ettlinger, Angew. Chem.,91, 748 (1979).
R. K. Howe, J. Am. Chem. Soc.,93, 3457 (1971).
H. Joshida, H. Matsuura, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn.,48, 2907 (1975).
R. Manske and J. Gosselek, Tetrahedron,31, 2121 (1975).
P. T. Keought and M. Grayson, J. Org. Chem.,29, 631 (1964).
A. Weissberger, E. Proskauer, J. Riddick, and E. E. Toops, Jr., Organic Solvents, 3rd ed., Wiley-Interscience, New York (1971).
S. Takahashi, L. A. Coheu, H. K. Miller, E. C. Peake, J. Org. Chem.,36, 1205 (1971).
A. M. Hamid and S. Trippet, J. Chem. Soc., C, 2625 (1967).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 456–459, February, 1988.
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Nesmeyanov, N.A., Kharitonov, V.G., Rebrova, O.A. et al. Z, E isomerization of alkoxypropenylphosphonium salts by the action of nucleophiles. Russ Chem Bull 37, 375–378 (1988). https://doi.org/10.1007/BF00957449
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DOI: https://doi.org/10.1007/BF00957449