75864-90-3Relevant academic research and scientific papers
Kinetics and Mechanism of the Reactions of Primary Amines with Pyrylium Cations
Katritzky, Alan R.,Manzo, Ruben H.
, p. 571 - 575 (2007/10/02)
The initial reaction of primary amines with pyrylium cations to give the ring-opened intermediate is fast for strongly basic amines and is base-catalysed for weak amines.Ring-closure of the intermediate to give the pyridinium derivative is subject to ster
The Synthesis and Reactions of Sterically Constrained Pyrylium and Pyridinium Salts
Katritzky, Alan R.,Thind, Sukhpal S.
, p. 1895 - 1900 (2007/10/02)
Efficient syntheses are developed for several pyrylium cations with substitution patterns more sterically demanding than 2,4,6-triphenyl and these are examined as reagents for the conversion of primary amino into a leaving group.The 2-mesityl-4,6-diphenyl derivative did not react smoothly with amines.The 2,6-di-t-butyl-4-phenyl-pyrylium cation gave the corresponding pyridinium derivatives, but they resisted nucleophilic attack. 2-t-Butyl-4,6-diphenylpyridinium cations suffer nucleophilic attack with about the same ease as the 2,4,6-triphenyl analogues.Dihydrobenzopyrylium (6) and tetrahydrodibenzoxanthylium cations (7) gave pyridinium cations which underwent much easier nucleophilic attack: thus they alkylate xanthate anion in ethanol solution and acetate anion in acetic acid.
The Preparation of Primary Alkyl and Benzyl Fluorides from the Corresponding Primary Amines
Katritzky, Alan R.,Patel, Ranjan C.
, p. 2901 - 2903 (2007/10/02)
N-substituted 2,4,6-triphenylpyridinium fluorides (in contrast to these and other tetrafluoroborates) thermolyse to the corresponding primary alkyl and benzyl fluorides.The pyridinium fluorides are made from 2,4,6-triphenylpyrylium fluoride and the relevant amine.
