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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ScarletDemiurge on November 21, 2021, 05:28:44 PM

Title: Can the ion bromonium be produced from NBS without HBr?
Post by: ScarletDemiurge on November 21, 2021, 05:28:44 PM

I'm trying to figure out the mechanism for this reaction (the product is in the second image). As far as I understand, it is an electrophilic aromatic substitution, but I don't understand how to get a bromonium ion out of the NBS. I read that the Br in an N-Br bond has a partial positive charge so could the triazole attack it directly? Or do I need to first separate the Br, turn it into a bromonium ion, and then attack that ion with the triazole? If so, does anyone know how to do that?

Title: Re: Can the ion bromonium be produced from NBS without HBr?
Post by: phth on November 21, 2021, 08:48:35 PM

Yes,
The sp2 nitrogens act as bases and create intermediates that generate a small concentration of reactive N⁺-Br and Br-Br--> product and succinimide (R2NH)