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chemrox
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Yes that would be a problem with alkane gasses wouldn;t it. @nicodem thanks for the merge sorry for doubling. I see the experience has been reduced
yields with aldehydes. I was working more recently with a ketone and got nearly theoretical yields in air with water removal. So if I can make the
imine and reduce it with NaBH4 in atmosphere does it follow the STAB procedure would work well in air with the same ketone? Or is there something
about taking the water out with acetic acid that makes the imine more labile to oxidation? This doesn't seem intuitively correct. ie if it works
with NaBH4/-H2O in air so should it be with STAB/acetic but since costly reagents are involved I definitely want as much real-world advice on this as
I can get.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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Methansaeuretier
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Btw. does STAB work also for dialkylation? Under which conditions?
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jon
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pretty much the same thing as reductive amination using primary amines.
only the double bond is on the carbon it's called an enamine.
it just occured to me STAB is'nt a way around azetropic distillation of the amine and the ketone because STAB is readily decomposed by water.
the only way around that is sodium cyano boro hydride.
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Methansaeuretier
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Quote: Originally posted by jon  | pretty much the same thing as reductive amination using primary amines.
only the double bond is on the carbon it's called an enamine.
it just occured to me STAB is'nt a way around azetropic distillation of the amine and the ketone because STAB is readily decomposed by water.
the only way around that is sodium cyano boro hydride. |
STAB does defenitly work also without azeotropic destillation. I've done it myself.
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jon
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good to know
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