Główne metody syntezy soli piryliowych

Günther, A.; Soroka, J. A.

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Tytuł artykułu

Główne metody syntezy soli piryliowych

Autorzy

Günther A. , Soroka J. A.

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Warianty tytułu

The main synthesis of pyrylium salts

Języki publikacji

Abstrakty

Pyrylium salts are valuable organic aromatic compounds based on pyrylium cation, which are built from six-membered ring and contain one positively charged oxygen atom. The presence of a non-nucleophilic anion makes aromatic system stable. These salts are very sensitive for nucleophiles and react with them easily, especially 2,6-disubstituted ( positions) salts because of a lower density of electrons than that of 4-substitued ( position). They react with primary amine groups giving pyridinium salts. This mechanism runs through the stages of attack of nucleophile, ring opening and ring closing (SnANRORC). The synthesis of pyrylium salts is very useful and comfortable because of their ionic properties, obtained products are not soluble in diethyl ether or liquid alkanes, and can be easy isolated and purified from a reaction mixture. Pyrylium salts have a wide range of applications, such as laser dyes, fluorescent dyes, biological and chemical sensors, reactive matrices for MALDI-MS imaging of biologically active primary amines (e.g. amphetamine, dopamine) and many others especially as a universal substrate in the synthesis of heterocyclic compounds. In nature pyrylium ions occur only in structures of anthocyanins in tissues of higher plants and are used as food dyes. Herein we described selected properties and applications of pyrylium salts, chemical reactivities, and the most frequently used and useful methods of syntheses of pyrylium salts which can be used as starting materials to obtain different class of heterocyclic compounds.

Słowa kluczowe

sole piryliowe kation piryliowy addycja nukleofilowa mechanizm SnANRORC

pyrylium salts pyrylium cation nucleophilic addictions mechanism SnANRORC

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2017

Tom

[Z] 71, 1-2

Strony

87--108

Opis fizyczny

Bibliogr. 53 poz., schem.

Twórcy

autor

Günther A.

andrzej.gunther@zut.edu.pl

Zachodniopomorski Uniwersytet Technologiczny w Szczecinie, Wydział Technologii i Inżynierii Chemicznej. Al. Piastów 42, Szczecin

autor

Soroka J. A.

jacek.soroka@zut.edu.pl

Zachodniopomorski Uniwersytet Technologiczny w Szczecinie, Wydział Technologii i Inżynierii Chemicznej. Al. Piastów 42, Szczecin

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Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).

Typ dokumentu

Bibliografia

Identyfikator YADDA

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