Abstract: Reactions of hexafluoro-1,4-naphthoquinone with phosphorus-centered bis-phenylphosphanes with structure Ph2P(CH2)(n)PPh2 (where n = 1-5) and Et2P(CH2)(2)PEt2 in various solvents (anhydrous C6H6, aq. C6H6, aq. dioxane, aq. DMSO, or MeOH) were investigated. It was shown that the use of aqueous dioxane and DMSO leads to target products of phosphanodefluorination (i.e., phosphorus-containing betaines and bis-betaines) with high yields. We found that the betaines upon purification by thin-layer chromatography underwent various transformations such as a ring contraction (thus yielding novel polyfluorinated indenones) or addition of an acetone molecule at the C=O bond of the fluorinated 1,4-naphthoquinone. According to X-ray diffraction analysis, there were intermolecular F center dot center dot center dot pi interactions in the crystal packing of all the obtained betaines. The interactions are characterized by short distances F center dot center dot center dot Cg from 3.151(5) to 3.831(2) angstrom (where Cg is a centroid of pi-system).

Cite: Zhivetyeva S.I. , Tretyakov E.V. , Bagryanskaya I.Y.
Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone
Journal of Fluorine Chemistry. 2018. V.206. P.19-28. DOI: 10.1016/j.jfluchem.2017.11.010 WOS Scopus РИНЦ

Dates:

Published print:

Feb 1, 2018

Identifiers:

Web of science	WOS:000424177300003
Scopus	2-s2.0-85037631631
Elibrary	35517331
OpenAlex	W2775631624

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