December 05, 2021, 08:53:51 AM
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Topic: Can the ion bromonium be produced from NBS without HBr?  (Read 139 times)

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Offline ScarletDemiurge

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Can the ion bromonium be produced from NBS without HBr?
« 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?

Offline phth

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Re: Can the ion bromonium be produced from NBS without HBr?
« Reply #1 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)

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