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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kukurbituril on July 05, 2011, 10:13:19 AM

Title: DMF as hydride donor
Post by: kukurbituril on July 05, 2011, 10:13:19 AM
Hello, here is the question: can DMF act as a hydride donor? If it is so, could you post some reference??
Title: Re: DMF as hydride donor
Post by: mickelcorleone on July 05, 2011, 01:10:44 PM
I think that NO :-\

Title: Re: DMF as hydride donor
Post by: Honclbrif on July 05, 2011, 03:25:37 PM
Can't say I've ever heard of DMF acting as a hydride donor, but formic acid can. What type of functional group are you trying to reduce?
Title: Re: DMF as hydride donor
Post by: kukurbituril on July 06, 2011, 03:51:31 PM
I´ve got a imide group in my molecule and in mass spectra I see the mass of 2 more then my desired product. So one hypothesis was that DMF can somehow act as a reducting agent (reaction is catalysed by palladium) and one carbonyl is reduced to hydroxyl.
Title: Re: DMF as hydride donor
Post by: Honclbrif on July 06, 2011, 04:30:52 PM
Have you run an IR or NMR on the substrate to confirm the reduction?
Title: Re: DMF as hydride donor
Post by: g-bones on July 13, 2011, 06:49:37 PM
If you obtained your mass spectrum via LCMS, the method of ionization is often through protonation.  Typically the eluent is a percentage of formic acid in water and DMF.  This maybe where you get your hyride.