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THE SYNTHESIS OF NEW PODAND, 1,8-BIS(9’-CARBAZOLYL)-3,6-DIOXAOCTANE

THE SYNTHESIS OF NEW PODAND, 1,8-BIS(9’-CARBAZOLYL)-3,6-DIOXAOCTANE

Abstract

The main kind of phase transfer catalysts are crown-esters, cryptands, quarternary ammonia salts and podands. The podand kind of phase transfer catalysts is the most efficient for the organic chemistry technologies. The aim of this investigation is the syntheses of new podand which consists of two carbazole moiety and triethylenglygol chain. The synthesis of 1,8-bis(9’-carbazolyl)-3,6-dioxaoctane has been proposed. This containing two carbazolyl moiety podand is stable in the alkali media. The reaction of the synthesis is carried out in the 1,4-dioxane solution. Carbazole reacts with excess of potassium hydroxide in the boiling solvent in the presence of tetrabutyl ammonia bromide. Then the hot solution of potassium salt of carbazole is filtered off. Then the reaction of potassium salt of carbazole with 1,8-dibromo-3,6-dioxaoctane is carried out in 1,4-dioxane solution. After that the reaction mixture is cooled. The obtaining potassium bromide is filtered off. The 1,4-dioxane reaction solution is evaporated at reduced pressure. The residue is washed by water and then it is dried at reduced pressure. Then the residue is extracted by boiling tetrachlorocarbon. The extract is evaporated at reduced pressure yielding the technical product. The crude product yield is 77 %. The solid residue was crystallized from benzene or ethanol yielding the pure product. The additional quantity of the product is obtained by the column chromatography of the filtrate residue. The overall yield of pure 1,8-bis(9’-carbazolyl)-3,6-dioxaoctane is 54 %. The melting point of 1,8-bis(9’-carbazolyl)-3,6-dioxaoctane is 128 – 129 °С. The product structure has been confirmed by data of NMR 1H spectra, NMR 13C spectra and mass-spectra.

Запропоновано метод синтезу нового подандного каталізатора міжфазного переносу, що містить дві карбазолільні групи та є стійким до дії лугів –1,8-Біс(9’-карбазоліл)-3,6-діоксаоктану. Поданд амінного типу був синтезований взаємодією 1,8-дибром-3,6-діоксаоктану з калієвою сіллю карбазолу. Доочищення продукту від залишків карбазолу відбувається при перекристалізації із бензену. Структура 1,8-біс(9’-карбазоліл)-3,6-діоксаоктану підтверджена за допомогою даних ЯМР 1Н, 13С – спектрів, а також мас-спектрів.

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
0
Average
Average
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