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Topic: Benzotriazole mechanism  (Read 9030 times)

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Offline BluePill

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Benzotriazole mechanism
« on: May 11, 2012, 08:59:40 AM »
I'm trying to figure out the mechanism for the synthesis of benzotriazole from diaminobenzene using diazotization.



and its rearrangement as well



Thoughts?
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Offline orgopete

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Re: Benzotriazole mechanism
« Reply #1 on: May 11, 2012, 07:13:00 PM »
I think I would draw out the nitrosation steps. The stereoelectronic of a cyclization from a diazonium salt do not look good to me. I would think the diazonium salt would couple rather than cyclize. I would be more inclined to think the ring formation occurs before the dehydration.
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Offline BluePill

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Re: Benzotriazole mechanism
« Reply #2 on: May 14, 2012, 01:30:30 AM »
Sorry I got busy this past few days. You mean something like this?

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