Can the ion bromonium be produced from NBS without HBr?

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

Post by ScarletDemiurge »

I'm trying to figure out the mechanism for this reaction
NBS.png
NBS.png (5.41 KiB) Viewed 66 times
(the product is in the second image
2021-11-21 (1).png
2021-11-21 (1).png (94.24 KiB) Viewed 66 times
). 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? I read that it can be done in the presence of HBr, but this reaction does not include HBr anywhere, so I'm not sure what happens there.
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ChenBeier
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Re: Can the ion bromonium be produced from NBS without HBr?

Post by ChenBeier »

So far I know it separates by hγ. Light.

https://www.masterorganicchemistry.com/ ... ccinimide/
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