Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: johnnyd on August 30, 2010, 02:41:56 PM

Title: Cleavage of N-tosyl group
Post by: johnnyd 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 :)

Title: Re: Cleavage of N-tosyl group
Post by: OC pro on September 05, 2010, 11:04:47 AM

KOH in EtOH. Stirring at room temperature should do the job.

Title: Re: Cleavage of N-tosyl group
Post by: OC pro 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!

Title: Re: Cleavage of N-tosyl group
Post by: johnnyd on September 08, 2010, 02:21:02 PM

Dude. This is awesome! Exactly what I was looking for! Thanks a million.

Title: Re: Cleavage of N-tosyl group
Post by: OC pro on September 09, 2010, 01:30:34 PM

No prob...that´s what a good forum is made for  ;D