72377-94-7Relevant academic research and scientific papers
Photostimulated Reactions of N,N-Disubstituted Amide Enolate Anions with Haloarenes by the SRN1 Mechanism in Liquid Ammonia
Rossi, Roberto A.,Alonso, Ruben A.
, p. 1239 - 1241 (1980)
The photostimulated reactions of chloro-, bromo-, and iodobenzenes, 1-chloronaphthalene, and 9-bromophenanthrene with the enolate anion of N-methyl-N-phenylacetamide in liquid ammonia gave good yields of substituted products.In the dark, iodobenzene gave 34percent of substitution product, but chlorobenzene did not react.The enolate anion of N,N-dimethylacetamide was only partially soluble in liquid ammonia, but good yields of substitution products were obtained.The enolate anion of N-acetylpiperidine was insoluble in liquid ammonia, but the enolate anion of N-acetylmorpholine was soluble and good yields of substitution products were obtained under photostimulation.It is suggested that these reactions occur by the SRN1 mechanism of aromatic substitution.
