Amines acridinium salts

The oxidative behaviour of the acridinium carbocations 61 was also explored by the group of Lacour in the photoinduced electron transfer reaction [160]. In the amount of 2 mol%, the achiral hindered acridinium salt 61 catalyzed the aerobic photooxidation of the primary benzylic amine to benzylimine in the yield of 74% (Scheme 63). 

Further extensions of the use of pyrylium salts as synthons have appeared for example, their reaction with hydrazines. The xanthyUum salt (27 A = 0) reacted with amines under very mild conditions and in good yield and it has been used to synthesize sulphones, sulphides, and ethers in the presence of phase-transfer catalysts for example, 2-hexyloxynaphthalene was obtained in 70% yield by heating the acridinium salt (27 A = NC Hia) with sodium 2-naphthoxide and Bu4N A phase-transfer catalyst has... 

N. Chupakhin, and maintained first his candidate thesis Elucidation of the oxidative condensation of aromatic amines with acridinium salts (related to nucleophilic substitution of hydrogen)... 

The conversion of primary amines into nitrate esters via the pyridinium salts (43) represents a considerable improvement over existing methodology (Scheme 58). By use of the corresponding acridinium salts (44) the method is also suitable for large-scale work, or for the preparation of high molecular weight nitrates or polynitrates (Scheme 59). 

The family of photoreducible dyes (e.g, acridinium, xanthene, thiazinium among other classes of dyes) produce excited states of essentially quinoidal structures which can act as efficient acceptors of electrons. Amines [59], sulfur compounds, especially sulfmate salts [60], heterocycles of low ionization potential [61], alkylcarboxylates and stable enolate anions [62], and several classes of organo-metallic compounds, notably allylic and benzylic organostannanes [63], represent classes of compounds which have proved efficacious as coinitiators in electron transfer sensitization with these dyes. Electron transfer with the organometallics was unambiguously established in a series of model studies involving electron acceptors of the anthracene class [64],... 

The aminoarylation of 9-methylacridinium salts with aromatic amines provides a well-established example of a SET from arylamines to the acridinium ion, as evidenced by the formation of diacridanyl and arylamine radical cation species (Scheme 62). Also, treatment of W-methylacridinium ion with W,W -tetramethyl-para-phenylenediamine, as the model compound, gave the characteristic color of the Wurster s Blue radical cation [11, 136, 137]. 

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