78018-93-6Relevant academic research and scientific papers
Identification of the Products of Solvolysis of N-Benzylpyridinium Cations in the Absence of Nucleophiles
Katritzky, Alan R.,Marson, Charles M.,Chen, Jen-Luan,Saczewski, Franciszek,King, Roy W.
, p. 1331 - 1336 (2007/10/02)
Mono-, tri-, and penta-cyclic N-benzylpyridinium tetrafluoroborates undergo tharmolysis in chlorobenzene as solvent to give products of benzylation both of the solvent and of the pyridine leaving group.Thermolysis alone, and in nitrobenzene as solvent, yielded mainly products of benzylation of the leaving group.The results support the previously postulated mechanism of unimolecular solvolysis of compounds of these types in non-polar solvents.
The Synthesis of Some Highly Strained Pyrylium and N-Benzylpyridinium Salts and Kinetics of their Reactions with Piperidine
Katritzky, Alan R.,Marson, Charles M.,Thind, Sukhpal S.,Ellison, Joan
, p. 487 - 496 (2007/10/02)
5,8-Dimethyl-1-tetralone (11) yields the hindered pyrylium salts (12)-(14), which give the corresponding pyridines and pyridinium salts with ammonia and amines.Chroman-4-one affords the oxoniaphenanthrene perchlorate (17).The additional steric hindrance f
Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 8. Conductimetric and Spectrophotometric Rate Constants for the Reactions of Pyridimium and Related Cations with Piperidine in Chlorobenzene
Katritzky, Alan R.,Ou, Yu Xiang,Ellison, Joan,Musumarra, Giuseppe
, p. 1421 - 1426 (2007/10/02)
A conductimetric method is developed to obtain rates for the title reactions for which the spectrophotometric method fails.It gives equivalent results.NN'-Dimethylthiourea displaces heterocyclic leaving groups at rates similar to those for piperidine.Compared with α-hydrogen, α-methyl groups render pyridine a less effective leaving group, whereas α-ethoxycarbonyl groups show a large rate enhancement.
Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. 2. N-Benzylpyridinium Cations: Rate Variation with Steric Effects in the Leaving Group
Katritzky, Alan R.,El-Mowafy, Azzahra M.,Musumarra, Giuseppe,Sakizadeh, Kumars,Sana-Ullah, Choudhry,et al.
, p. 3823 - 3830 (2007/10/02)
N-Benzyl groups are transferred to piperidine from pyridinium ions by unimolecular SN1 and/or bimolecular SN2 mechanisms.Steric acceleration by α-phenyl groups is reduced by an adjacent β-methyl group but increased by constraining th
