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Topic: Cyclization of diamine with aldehyde  (Read 3857 times)

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Offline Rutherford

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Cyclization of diamine with aldehyde
« on: July 04, 2013, 09:47:03 AM »
I don't understand why is the second -NHMe in the picture, at first below and then above the plane. Can someone explain me what actually happened there and why? The mechanism is attached.
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Offline discodermolide

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Re: Cyclization of diamine with aldehyde
« Reply #1 on: July 04, 2013, 09:59:22 AM »
Well if the amine remained below the plane it could not form the C-N bond with elimination of water. So the bond rotates to bring the amine above the plane and hence reaction occurs.
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Offline Rutherford

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Re: Cyclization of diamine with aldehyde
« Reply #2 on: July 04, 2013, 10:06:50 AM »
Why it couldn't if the first one could?
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Offline discodermolide

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Re: Cyclization of diamine with aldehyde
« Reply #3 on: July 04, 2013, 10:52:31 AM »
Either one can react first, the second will then undergo the rotation and cyclisation.
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Offline Rutherford

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Re: Cyclization of diamine with aldehyde
« Reply #4 on: July 04, 2013, 11:10:46 AM »
Ok, understood. Thanks very much.
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