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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: alphahydroxy on May 18, 2009, 05:51:28 PM

Title: Using DMF as an electrophile
Post by: alphahydroxy on May 18, 2009, 05:51:28 PM

I wonder if someone could help me!

I'm having a bit of a dumb moment, and I can't seem to draw out the mechanism for the use of DMF as an aldehyde equivalent... Could someone please draw it out for me ?!

Thanks!

Title: Re: Using DMF as an electrophile
Post by: azmanam on May 19, 2009, 07:07:31 AM

try these.  You don't necessarily need POCl3, but I think you'll get the idea

http://en.wikipedia.org/wiki/Vilsmeier-Haack_reaction
http://www.organic-chemistry.org/namedreactions/vilsmeier-reaction.shtm

Title: Re: Using DMF as an electrophile
Post by: alphahydroxy on May 21, 2009, 10:30:35 AM

Thanks for that!

I do already know of the Vilsmeier-Haack and was looking for the use of DMF without POCl₃ in particular.

If anyone is interested, the reaction is called the Bouveault aldehyde synthesis, and it goes a little something like this! (http://en.wikipedia.org/wiki/Bouveault_aldehyde_synthesis)