Welcome to LookChem.com Sign In|Join Free

Article Doi

Aminoketone Enolisation: Influence of Increasing Chain Length on Intramolecular Catalysis

DOI: 10.1039/P29880000163

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 163 - 168 (1988)

Update date:2022-08-02

Topics:

Authors:

Cox, Brian G.Cox, Brian G.

Maria, Paolo DeMaria, Paolo De

Guerzoni, LorenzaGuerzoni, Lorenza

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P29880000163

Kinetic results are reported on the rates of ionisation of piperidino- and morpholino-phenones of varying chain length in buffer and dilute hydroxide solution, as measured by their rates of halogenation.For both series of aminoketones two important factors are responsible for a high reactivity relative to acetophenone: the positive charge on the protonated (and N-methylated) derivatives, which has a strong influence in the α-(n=1) and β-(n=2) position, and intramolecular general base catalysis by the neutral amino group, which has a maximum effect for the δ-(n=4) derivative.Results for the more acidic protonated morpholinoketones are almost identical to those of corresponding piperidinoketones and show no evidence of intramolecular general acid catalysis.The reduced basicity of the morpholino group is reflected in lower rate constants for the intramolecular general base-catalysed reaction.

View More

Products guided by the article

Product name:4-Methyl-4-(4-oxo-4-phenyl-butyl)-morpholin-4-ium; iodide

Cas No:116849-56-0

116849-56-0

R&D Labs maybe for 116849-56-0

Relevant to this article

Hot Product