100143-75-7Relevant academic research and scientific papers
Products and Mechanisms of the Reactions of Methyl 4-Nirtobenzyl Ether with N-Bromosuccinimide, N-Bromotetramethylsuccinimide and the N-Bromotetramethylsuccinimide-Tetrabutylammonium Tetramethylsuccinimide Complex
Eberson, Lennart,Finkelstein, Manuel,Hart, Shirly A.,Ross, Sidney D.
, p. 1000 - 1003 (2007/10/02)
The reactions of methyl 4-nitrobenzyl ether with N-bromosuccinimide, N-bromotetramethylsuccinimide and the N-bromotetramethylsuccinimide-tetrabutylammonium tetramethylsuccinimide complex have been studied.The formation of imidosubstituted ethers with all three reagents is attributed to ionic mechanisms.In the case of the complex, the mechanism involves base-catalyzed bromination of the substrate followed by nucleophilic substitution by the tetramethylsuccinimide anion.Imido substitution by N-bromoimides alone seems to be limited to substrates, RH, which correspond to stable carbocations, R+, such as α-oxy- and α-aza-carbocations, trityl cation and tropylium ion.
