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

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

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2018, Том: 206, Страницы: 19-28 Страниц : 10 DOI: 10.1016/j.jfluchem.2017.11.010

Ключевые слова

Fluorinated 1,4-naphthoquinones; Bis-phosphanes; Nucleophilic substitution; Phosphonium betaines

Авторы

Zhivetyeva S.I. ¹ , Tretyakov E.V. ^1,2 , Bagryanskaya I.Yu. ^1,2

Организации

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosthirsk State Univ, Natl Res Univ, Novosibirsk 630090, Russia

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).

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 OpenAlex

Опубликована в печати:

1 февр. 2018 г.

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

БД	Цитирований
Web of science	6
Scopus	5
OpenAlex	5