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Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone. / Zhivetyeva, S. I.; Tretyakov, E. V.; Bagryanskaya, I. Yu.

In: Journal of Fluorine Chemistry, Vol. 206, 01.02.2018, p. 19-28.

Research output: Contribution to journal › Article › peer-review

Harvard

Zhivetyeva, SI, Tretyakov, EV & Bagryanskaya, IY 2018, 'Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone', Journal of Fluorine Chemistry, vol. 206, pp. 19-28. https://doi.org/10.1016/j.jfluchem.2017.11.010

APA

Zhivetyeva, S. I., Tretyakov, E. V., & Bagryanskaya, I. Y. (2018). Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone. Journal of Fluorine Chemistry, 206, 19-28. https://doi.org/10.1016/j.jfluchem.2017.11.010

Vancouver

Zhivetyeva SI, Tretyakov EV, Bagryanskaya IY. Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone. Journal of Fluorine Chemistry. 2018 Feb 1;206:19-28. doi: 10.1016/j.jfluchem.2017.11.010

Author

Zhivetyeva, S. I. ; Tretyakov, E. V. ; Bagryanskaya, I. Yu. / Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone. In: Journal of Fluorine Chemistry. 2018 ; Vol. 206. pp. 19-28.

BibTeX

@article{ef5d96acb5424864b704957c46b667fc,
title = "Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone",
abstract = "Reactions of hexafluoro-1,4-naphthoquinone with phosphorus-centered bis-phenylphosphanes with structure Ph2P(CH2)nPPh2 (where n = 1–5) and Et2P(CH2)2PEt2 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[dbnd]O bond of the fluorinated 1,4-naphthoquinone. According to X-ray diffraction analysis, there were intermolecular F⋯π interactions in the crystal packing of all the obtained betaines. The interactions are characterized by short distances F⋯Cg from 3.151(5) to 3.831(2) {\AA} (where Cg is a centroid of π-system).",
keywords = "Bis-phosphanes, Fluorinated 1,4-naphthoquinones, Nucleophilic substitution, Phosphonium betaines, 1,4-NAPHTHOQUINONE, AUTOXIDATION, HYDROXY-QUINONES, HYDROXYQUINONES, CDC25, CHEMISTRY, AGENTS, INHIBITOR, DERIVATIVES, CYTOTOXICITY",
author = "Zhivetyeva, {S. I.} and Tretyakov, {E. V.} and Bagryanskaya, {I. Yu}",
note = "Publisher Copyright: {\textcopyright} 2017 Elsevier B.V.",
year = "2018",
month = feb,
day = "1",
doi = "10.1016/j.jfluchem.2017.11.010",
language = "English",
volume = "206",
pages = "19--28",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of novel phosphonium betaines and bis-betaines derived from hexafluoro-1,4-naphthoquinone

AU - Zhivetyeva, S. I.

AU - Tretyakov, E. V.

AU - Bagryanskaya, I. Yu

N1 - Publisher Copyright: © 2017 Elsevier B.V.

PY - 2018/2/1

Y1 - 2018/2/1

N2 - Reactions of hexafluoro-1,4-naphthoquinone with phosphorus-centered bis-phenylphosphanes with structure Ph2P(CH2)nPPh2 (where n = 1–5) and Et2P(CH2)2PEt2 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[dbnd]O bond of the fluorinated 1,4-naphthoquinone. According to X-ray diffraction analysis, there were intermolecular F⋯π interactions in the crystal packing of all the obtained betaines. The interactions are characterized by short distances F⋯Cg from 3.151(5) to 3.831(2) Å (where Cg is a centroid of π-system).

AB - Reactions of hexafluoro-1,4-naphthoquinone with phosphorus-centered bis-phenylphosphanes with structure Ph2P(CH2)nPPh2 (where n = 1–5) and Et2P(CH2)2PEt2 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[dbnd]O bond of the fluorinated 1,4-naphthoquinone. According to X-ray diffraction analysis, there were intermolecular F⋯π interactions in the crystal packing of all the obtained betaines. The interactions are characterized by short distances F⋯Cg from 3.151(5) to 3.831(2) Å (where Cg is a centroid of π-system).

KW - Bis-phosphanes

KW - Fluorinated 1,4-naphthoquinones

KW - Nucleophilic substitution

KW - Phosphonium betaines

KW - 1,4-NAPHTHOQUINONE

KW - AUTOXIDATION

KW - HYDROXY-QUINONES

KW - HYDROXYQUINONES

KW - CDC25

KW - CHEMISTRY

KW - AGENTS

KW - INHIBITOR

KW - DERIVATIVES

KW - CYTOTOXICITY

UR - http://www.scopus.com/inward/record.url?scp=85037631631&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2017.11.010

DO - 10.1016/j.jfluchem.2017.11.010

M3 - Article

AN - SCOPUS:85037631631

VL - 206

SP - 19

EP - 28

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 9160541