Kinetics of peroxodisulfate oxidation of ortho-substituted N,N-dimethylanilines, and the mechanism of Boyland-Sims oxidation was written by Srinivasan, Chockalingam;Perumal, Subbu;Arumugam, Natesan. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1985.Application In Synthesis of 2-Chloro-N,N-dimethylaniline This article mentions the following:
The kinetics of oxidation of o-RC6H4NMe2 (I; R = H, MeO, Me, F, Cl, Br, NO2) by S2O82- were studied in 50% (volume/volume) H2O-EtOH containing 0.025 mol/dm3 phosphate buffer (pH 7). The reaction is 2nd-order overall, and 1st-order in each reactant. The rate was not influenced by the presence of the free-radical inhibitor H2C:CHCH2OAc. An increase in the polarity of the medium enhances the rate. The reactivities of I lie in the order H > Me ≈ MeO > F > Br > Cl > NO2. Multiple regression anal. of the rate data reveals that the rate is susceptible to significant electronic and steric effects. All these observations are rationalized on the basis of attack of the oxidant at the ipso-position of the amine. Correlation anal. of reactivity data from the literature also indicates that the mechanism involves ipso-attack and not attack on N. In the experiment, the researchers used many compounds, for example, 2-Chloro-N,N-dimethylaniline (cas: 698-01-1Application In Synthesis of 2-Chloro-N,N-dimethylaniline).
2-Chloro-N,N-dimethylaniline (cas: 698-01-1) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Application In Synthesis of 2-Chloro-N,N-dimethylaniline
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics