Conclusions
-
1.
Reaction of triethylamine with the mixed anhydride of α-hydrohexafluoroisobutyric and benzoic acids results in cleavage of an α-proton to form a salt containing a mesomeric carbanion which is stable at temperatures below −40°C.
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2.
Cleavage of the triethylammonium salt of the mixed anhydride of α-hydrohexafluoroisobutyric and benzoic acids to benzoyl fluoride and a salt of trifluoromethylmalonyl difluoride involves several reversible elimination-addition steps of fluoride and triethylammonium benzoate, together with irreversible cleavage of the acid fluoride and mixed anhydride of α-hydro-β-benzoyloxypentafluoroisobutyric acid.
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3.
According to the19F NMR spectrum, the triethylammonium salt of trifluoromethylmalonyl difluoride at temperatures below −50°C contains three isomers as a result of restricted rotation around the partial double bonds
in the mesomeric carbanion.
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E. M. Rokhlin, A. Yu. Volkonskii, and E. I. Mysov, Izv. Akad. Nauk SSSR, Ser. Khim., 1359 (1978).
M. V. Urushadze, P. O. Okulevich, I. D. Rubin, P. V. Petrovskii,É. I. Fedin, E. M. Rokhlin, Yu. A. Cheburkov. and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 1137 (1972).
E. M. Rokhlin, E. G. Abduganiev, and U. Utebaev, Usp. Khim.,45, 1177 (1976).
I. L. Knunyants, L. T. Lantseva, É. P. Lur'e, and Yu. V. Zeifman, Izv. Akad. Nauk SSSR, Ser. Khim., 231 (1977).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1352–1359, June, 1932.
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Volkonskii, A.Y., Rokhlin, E.M. Mechanism of the cleavage of mixed anhydrides of α-hydrohexafluoroisobutyric acid by triethylamine. Russ Chem Bull 31, 1205–1210 (1982). https://doi.org/10.1007/BF00955980
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DOI: https://doi.org/10.1007/BF00955980