[JustaNovice]

I'm attempting to perform a Mitsunobu reaction with a phenol and ethylene glycol. Every reference I've read suggests it should work (however, after posting my difficulties here in the forum, I'm beginning to think that may be an incorrect suggestion). Anyways, I'm wondering if my DIAD reagent has oxidized. Does anyone have any suggestions on how to determine the sanctity of my DIAD?

Thanks as always.

[the.khemist.ds]

Hi,

My best suggestion is that you use the reagent to perform a simple Mitsunobu reaction that you know should work well. If the reaction doesn't work, it implies that the reagent is no-longer active.

If you are looking for some robust procedures you might be interested in some of the reactions listed on ChemSpider Synthetic Pages
http://cssp.chemspider.com/Search.aspx?q=mitsinobu

Dave

[JustaNovice]

Ok, thanks for the suggestion Dave. I appreciate it.

[Dan]

Get an NMR and compare with the lit (or the spectrum on the Sigma-Aldrich website).

[Honclbrif]

In addition to NMR, I like to take an IR too when assessing the quality of a reagent.