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Can the ion bromonium be produced from NBS without HBr?

Posted: Sun Nov 21, 2021 4:07 pm
by ScarletDemiurge
I'm trying to figure out the mechanism for this reaction
NBS.png
NBS.png (5.41 KiB) Viewed 1800 times
(the product is in the second image
2021-11-21 (1).png
2021-11-21 (1).png (94.24 KiB) Viewed 1800 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.

Re: Can the ion bromonium be produced from NBS without HBr?

Posted: Mon Nov 22, 2021 1:02 am
by ChenBeier
So far I know it separates by hγ. Light.

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