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Topic: Difficulty naming this rearrangement  (Read 4907 times)

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Offline Eddzzz_2012

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Difficulty naming this rearrangement
« on: February 12, 2013, 09:21:46 AM »
I'm having trouble naming this rearrangement so I know how to do the mechanism. Any help is appreciated. Cheers,

Ed
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Offline Dan

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Re: Difficulty naming this rearrangement
« Reply #1 on: February 12, 2013, 01:04:49 PM »
Quote from: Eddzzz_2012 on February 12, 2013, 09:21:46 AM
I'm having trouble naming this rearrangement so I know how to do the mechanism

You would learn more by trying to figure out the mechanism, rather than trying to remember the name so you can just look it up.

KOH is a base, phthalimide is relatively acidic.
What kind of a reagent is Br2 (acid/base/electrophile/nucleophile?)
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Offline orgopete

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Re: Difficulty naming this rearrangement
« Reply #2 on: February 12, 2013, 06:03:57 PM »
It looks like a Hofmann rearrangement.
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Offline Dan

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Re: Difficulty naming this rearrangement
« Reply #3 on: February 12, 2013, 07:03:53 PM »
Never mind...
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Offline orgopete

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Re: Difficulty naming this rearrangement
« Reply #4 on: February 13, 2013, 08:43:53 AM »
Quote from: Dan on February 12, 2013, 07:03:53 PM
Never mind...

I gave the name because I did not think it was obvious how the named reaction would lead to isatoic anhydride or anthranilic acid.
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Offline Eddzzz_2012

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Re: Difficulty naming this rearrangement
« Reply #5 on: February 13, 2013, 09:26:59 AM »
Cheers for the answers. I was thinking the Hofmann but I thought it was only for primary amides not secondary like this one, even though it has the same catalyst.
« Last Edit: February 13, 2013, 10:02:04 AM by Eddzzz_2012 »
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Offline Eddzzz_2012

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Re: Difficulty naming this rearrangement
« Reply #6 on: February 13, 2013, 10:50:33 AM »
so this means I have to convert this into a primary amide by attacking the carbonyl group with an OH.
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Offline Eddzzz_2012

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Re: Difficulty naming this rearrangement
« Reply #7 on: February 13, 2013, 12:41:52 PM »
Cheers, got this in the end!
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