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java
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Dakin-West Reaction.........
Mon May 23, 2005 12:01 am |
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Dakin-West Reaction.........which may be a potential route to go fast , also sodium acetate can replace the pyridine base needed in the reaction....java
\...........so the reaction seems to need removal of HCHO and a catalytic reduction with Pd to reduce tha amide to a methylamine, yes it may sound like wishful thinking but one has to have a base to start from to make any dreams come true......java
Last edited by java on Sat Jun 11, 2005 2:16 am; edited 4 times in total |
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re: Dakin-West Reaction.........
Thu Jun 09, 2005 4:24 am |
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I have a reaction that requires the removal of the HCHO(formaldehyde) from a ketone , hence in a Dakin -West reaction the amino acid Phenylalanine is treated with GAA will make an ozaxolone, meaning a ketone where the carboxylic acid active group formerly resided and an amide where the amine group formerly resided. The task is to remove the formaldeyde to leave the alkane and the amide in place, later the amide can be reduced to a methylamine and hence methedrine in a not too laborious method.......any ideas on the task laid before you?..................java |
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re: Dakin-West Reaction.........
Tue Jun 14, 2005 3:37 am |
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Maybe there is a way to convert the ketone to an aldehyde hence making easier to remove than an alcohol and the task is to reduced the aldehyde to the hydrocarbon.
Here is an interesting finding an enzyme that will convert aldehydes to ketones or ketones to aldehydes.....
" Beta Barrel Enzymes :many enzymes use the beta barrel shape to form their active site.
Let's look at two examples of those type of enzymes. First, Triose-P Isomerase (TIM), which
catalyzes the conversion of an aldehyde to a ketone. How does the 'perfect enzyme' work?
Aldehydes are converted to ketones or ketones to aldehydes, via an endiol intermediate. "
I'm looking for a catalytic hydrogenation to reduce the aldehyde to the hydrocarbon, if Pd works it will also reduce the acylated amine group hence give us the desired methylated aromatic amine, but then I think it will only reduce the alsehyde to an alcohol,..............and of course the Clemmensen Reduction: Carbonyl compounds can also be reduced by the Clemmensen reduction using zinc-mercury amalgam in the presence of hydrochloric acid; the mechanism most likely involves free radicals, which will give the hydrocarbon desired..........java |
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re: Dakin-West Reaction.........
Mon Jul 04, 2005 3:04 am |
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While my computer was down for a couple of weeks I hit the books and tried to resolve the ketone removal of this equation and ran into some interesting material in March's 5th ed. page 318, .....through some photochemistry ketones can be processed through type I cleavage in the Norrish Type I cleavage
...............HV
R'-CO-R -------> R'-CO- + R
so that we loose the carbon and the remainder can be catalytically hydrogenated and reduced to the desired aromatic amine.
It seems interesting enough , though some reading required to figure out what happens, so pick up a copy of March's 5th ed. over at the reference section and see if we can resolve this thing once and for all.................java |
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