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Simultaneous Formation of Cage and Spirane Pentaalkoxyphosphoranes in Reaction of 5,5-Dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphosphorinane with Hexafluoroacetone

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Abstract

The reaction of hexafluoroacetone with 5,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphosphorinane occurs in two simultaneous directions: through the formation of cage phosphorane and spirophosphorane—1,1-(2,2-dimethylpropylenedioxy)-4,5-diphenyl-3,3-bis(trifluoromethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.11.4]heptane and 2-(2,2-dimethylpropylenedioxy)-2-hexafluoroisopropoxy-4,5-diphenyl-1,3,2-dioxaphospholene, respectively. The latter was obtained by authentic synthesis from 2-hexafluoroisopropoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane and benzil. The mild hydrolysis of the compounds obtained leads to the formation of cyclic phosphates. The structure of the obtained compounds was determined by the NMR and mass spectrometry methods.

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This work was financially supported by the Russian Foundation for Basic Research (grant no. 19-03-00730).

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  1. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    V. F. Mironov & M. N. Dimukhametov

  2. Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    V. F. Mironov, Ya. S. Blinova & F. Kh. Karataeva

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Mironov, V.F., Dimukhametov, M.N., Blinova, Y.S. et al. Simultaneous Formation of Cage and Spirane Pentaalkoxyphosphoranes in Reaction of 5,5-Dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphosphorinane with Hexafluoroacetone. Russ J Gen Chem 90, 2080–2092 (2020). https://doi.org/10.1134/S1070363220110109

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