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Topic: Cleavage of N-tosyl group  (Read 5201 times)

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Offline johnnyd

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Cleavage of N-tosyl group
« on: August 30, 2010, 02:41:56 PM »
Has anyone done one of these for an N-tosyl aziridine? Is it possible? Any help appreciated :)
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Offline OC pro

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Re: Cleavage of N-tosyl group
« Reply #1 on: September 05, 2010, 11:04:47 AM »
KOH in EtOH. Stirring at room temperature should do the job.
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Offline OC pro

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Re: Cleavage of N-tosyl group
« Reply #2 on: September 06, 2010, 02:19:49 PM »
I have found an even better procedure which is suitable for aziridines:

Organic Letters 2009, pages 503-506

The procedure is as follows (very simple): dissolve 1equiv. of the tosylamide THF. Add Water (18equiv.) and pyrrolidine (12equiv.). Then add samarium diiodide (SmI2, 6equiv.) and stir at room temperature. Reactions are finished within SECONDS!
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Offline johnnyd

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Re: Cleavage of N-tosyl group
« Reply #3 on: September 08, 2010, 02:21:02 PM »
Dude. This is awesome! Exactly what I was looking for! Thanks a million.
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Offline OC pro

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Re: Cleavage of N-tosyl group
« Reply #4 on: September 09, 2010, 01:30:34 PM »
No prob...that´s what a good forum is made for  ;D
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