SN2 Substitution Reactions at the Amide Nitrogen in the Anomeric Mutagens, N-Acyloxy-N-alkoxyamides was written by Cavanagh, Katie L.;Glover, Stephen A.;Price, Helen L.;Schumacher, Rhiannon R.. And the article was included in Australian Journal of Chemistry in 2009.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:
N-Acyloxy-N-alkoxyamides 1a are unusual anomeric amides that are pyramidal at the nitrogen because of bis oxyl substitution. Through this configuration, they lose most of their amide character and resemble α-haloketones in reactivity. They are susceptible to SN2 reactions at nitrogen, a process that is responsible for their mutagenic behavior. Kinetic studies have been carried out with the nucleophile N-methylaniline that show that, like SN2 reactions at carbon centers, the rate constant for SN2 displacement of carboxylate is lowered by branching β to the nitrogen center, or bulky groups on the alkoxyl side chain. Branching or bulky groups on the carboxylate leaving group, however, do not impact on the rate of substitution, which is mostly controlled by the pKA of the departing carboxylate group. These results are in line with computed properties for the model reaction of ammonia with N-acetoxy-N-methoxyacetamide but are in contrast to the role of steric effects on their mutagenicity. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene).
2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary