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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: HoustonS on October 28, 2005, 11:06:37 AM

Title: protecting group on imine
Post by: HoustonS on October 28, 2005, 11:06:37 AM

hi there,

is it possible to protect an imine the same way you can protect a ketone with ho/\/oh and h+?
also, in a synthesis, is it possible to use imines as intermediates (made from ketones), or is the reaction just too unfavorable?

THANKS!

Title: Re:protecting group on imine
Post by: movies on October 28, 2005, 02:09:46 PM

Some imines are very stable and can be isolated, some you can even purchase from Aldrich.  The proecting group question is a little different though.  In order to reveal the imine you would have to cleave the protecting group in the presence of something like ammonia and you would have to run the reaction anhydrous to prevent water from hydrolyzing the imine (or an intermediate) to the carbonyl compound.  Since the cleavage of acetal protecting groups usually requires relatively acidic conditions, running the reaction in ammonia isn't really an option.