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Topic: Fluorosuccinimide  (Read 6480 times)

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Offline Urbanium

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Fluorosuccinimide
« on: August 19, 2014, 05:19:38 AM »
Does anyone know why is N-fluorosuccinimide (201281-58-5) such uncommon reagent for fluorination? I checked some major suppliers and none of them sells it.

How could I prepare/obtain it? If anyone could cite some reference with synthesis procedure I'd be Grateful, since SciFinder didn't help me a lot, but there are papers citing use of it.

Offline Dan

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Re: Fluorosuccinimide
« Reply #1 on: August 19, 2014, 07:57:22 AM »
there are papers citing use of it.

I've never seen it used - can you post the citations for some articles that use it?
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Offline Urbanium

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Re: Fluorosuccinimide
« Reply #2 on: August 20, 2014, 06:04:35 AM »
Some of these I found on SciFinder are:

Mohar, B; Sterk, D; Ferron, L; Cahard, D, Tetrahedron Letters, 2005, 46, 30, 5029-5031

Yang, Y; Su, C; Huang, X; Liu, Q Y; Tetrahedron Letters, 2009, 50, 41, 5754-5756

Chang, M-Y; Lee, M-F; Lin, C-H; Lee, N-C; Tetrahedron Letters, 2011, 52, 7, 826-829

But even if we ignore these papers above, is anyone familiar with use of NFSI? I just need a procedure for preparation.

Offline Hunter2

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Re: Fluorosuccinimide
« Reply #3 on: August 20, 2014, 07:50:07 AM »
In my knowledge N-Halogenesuccinimide  are obtained by reacting of Succinimide with the halogen itself. This isalid for Chlorine, Bromine and Iodine. Flourine is to reactive. For the fluorine component The Iodinesuccinimide can be treated with silvwerflouride to exchange the halogene.

The other option is to treat N_Hydroxysuccinimide with Thionylflouride or Phosphoroustriflouride.

Offline Dan

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Re: Fluorosuccinimide
« Reply #4 on: August 20, 2014, 05:08:34 PM »
But even if we ignore these papers above, is anyone familiar with use of NFSI? I just need a procedure for preparation.

NFSI = N-Fluorobenzenesulfonimide (which you can buy) not N-fluorosuccinimide.
« Last Edit: August 21, 2014, 03:50:01 AM by Dan »
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