79719-35-0Relevant academic research and scientific papers
Nucleophilic addition and displacement in the reaction of 2,4,6-trimethylphenoxide ion with 1,3,5-trinitrobenzene. An oxigen-bonded aryloxide ?-complex
Buncel, Erwin,Moir, Robert Y.,Norris, Albert R.,Chatrousse, Alain-Pierre
, p. 2470 - 2474 (2007/10/02)
Reaction of 1,3,5-trinitrobenzene with potassium 2,4,6-trimethylphenoxide in dimethyl sulfoxide solution leads to ?-complex formation concurrently with displacement of a nitro group.The results provide definitive evidence for ?-complex formation via the oxigen of aryloxide ion in this system, and contrast with the situation that obtains with phenoxide ion itself, which under corresponding conditions yields the carbon-bonded ?-complex as the product of thermodynamic control.Stereoelectronic factors in ?-complex formation and in the diaryl ether resulting from nitro displacement are also discussed.
