ChemInform Abstract: Synthesis of 4‐Tosyloxy‐2‐substituted Phenols Using New Solid Pyridinium Salt Supported [Hydroxyl(tosyloxy)iodo]benzene Reagents.
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Abstract The pyridinium salt can be easily regenerated by MCPBA and Tos‐OH.2-Pyridone
Pyridinium Compounds
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Imidazo[1,5-a]pyridinium derivatives are easily synthesized by reaction of pyridinium triflates in pure isocyanide. The compounds obtained by treatment of pyridinium, 1,10-phenanthrolinium and 2,2′-bipyridinium triflates with tert-butyl isocyanide are described, along with the crystal structures of the latter two.
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Abstract Thirty‐three crystalline urethanes were prepared by the condensation of the new reagent, 3:5‐dinitro‐4‐methyl‐benzazide, in boiling ligroin solution with various phenols. The very high yields of the 3:5‐dinitro‐4‐methylphenyl‐urethanes obtained from the reaction and the excellent properties of these derivatives, indicated that 3:5‐dinitro‐4‐methyl‐benzazide is an excellent micro‐reagent for the identification of phenols.
Condensation reaction
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Attempts to synthesise thiazolo[3,4-a]pyridinium salts (3) and isothiazolo[2,3-a]pyridinium salts (2) by dehydration with boiling acetic anhydride of the 5,6,7,8-tetrahydro-8-oxothiazolo[3,4-a]pyridinium salts (11) and (12) and of the 4,5,6,7-tetrahydro-4-oxoisothiazolo[2,3-a]pyridinium salt (6) respectively are reported. The reasons for the failure of the aromatisation are discussed. 7-Bromo-8-hydroxy-3-methylthiazolo[3,4-a]pyridinium bromide (17) has been prepared by an alternative route.
Pyridinium Compounds
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In the presence of amines, the degradation of glutaconaldehyde in acidic medium can be prevented. By exploitation of this behavior, primary amines are transformed into their corresponding pyridinium salts, including those substrates that remain unreactive toward the Zincke salt, which is the reagent typically used to perform this transformation. The use of glutaconaldehyde also allows control of the nature of the counterion of the pyridinium with no need for additional salt metathesis reaction.
Primary (astronomy)
Salt metathesis reaction
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1-[Bis(dimethylamino)cyclopropenylio]pyridinium salt 6 reacts with activated methylene compounds 7 in the presence of pyridine to give triafulvenes 8. The use of 1,1′-oxy-di[2,3-bis(dimethylamino)cyclopropenylium] salt 5 for the same purpose is limited: with the ambident anions of 1,3-diketones, enol ether salts 9 are formed in some cases at the complete expense of triafulvenes 8. Compound 8n, however, can be obtained only from 5.
Methylene
Enol ether
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Nitration of the imidazo[1,2-a]pyridines (1) or (2), or (5) or (6), and (9) with nitric and sulphuric acids gives the pyridinium dinitromethylides (4a), (8), and (10), respectively, in which the pyridinium and dinitromethylide groups are orthogonal.
Nitric acid
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Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents.
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Cationic polymerization
Pyridinium Compounds
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N-alkylation of a novel pyridine sensor results in pyridinium salts whose conformations are stabilised by pyridinium cation-π interactions resulting in a fluorescent response that can be used to sense the presence of alkylating agents in solution at low concentration.
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