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Topic: Mechanism between dibromopentane and hydroxylamine  (Read 2360 times)

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Offline rotary1992

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Mechanism between dibromopentane and hydroxylamine
« on: March 15, 2013, 06:37:24 PM »
Hi guys, just wondering if any of you can suggest a mechanism for the reaction of dibromopentane with hydroxylamine (in the presence of base) to give n-hydroxypiperidine (piperidin-1-ol). any help would be appreciated. Thanks !
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Offline sjb

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Re: Mechanism between dibromopentane and hydroxylamine
« Reply #1 on: March 15, 2013, 06:42:28 PM »
Quote from: rotary1992 on March 15, 2013, 06:37:24 PM
Hi guys, just wondering if any of you can suggest a mechanism for the reaction of dibromopentane with hydroxylamine to give n-hydroxypiperidine (piperidin-1-ol). any help would be appreciated. Thanks !

Can you identify any potential bond formations / breakages that may form your product?
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Offline rotary1992

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Re: Mechanism between dibromopentane and hydroxylamine
« Reply #2 on: March 15, 2013, 06:47:22 PM »
I assume the C-Br bond breaks leaving a nucleophilic carbon. There is then a reaction of said C with N of hydoxylamine. I am unsure on how the mechanism proceeds to form cyclic piperidine. any suggestions?
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Offline Dan

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Re: Mechanism between dibromopentane and hydroxylamine
« Reply #3 on: March 16, 2013, 05:09:57 AM »
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