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Author: Subject: 3-phenyl-1,1,1-triflouroacetone
Flip
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[*] posted on 27-3-2006 at 23:20
3-phenyl-1,1,1-triflouroacetone


I ran across 3-phenyl-1,1,1-triflouroacetone in a catalog. aka. benzyl trifluoromethyl ketone, or 1,1,1-trifluoro-3-phenyl-2-propanone.

I can't help but wonder... is there anything I can do with this molecule synthetically. Is there perhaps a good way to remove the three terminal flourines? ;)

Wishful thinking probably.
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Lord_Worm
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[*] posted on 31-3-2006 at 16:50


hahah wat u trying to get.Phenylacetone
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Sandmeyer
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[*] posted on 31-3-2006 at 17:16


if you ever sucseed in doing this - send your synthesis to The Journal of Unpublished Chemistry, latest issue features:


The total synthesis of triethyl ammonium hydrobromide from expensive, difficult to prepare starting materials.

Abstract: Triethyl ammonium hydrobromide was synthesised in excellent yield from N-tertbutyldimethylsilanyl-4-bromo azetidinone in a single step.

http://jun.lemonie.net/NEt3HBr.html




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stoichiometric_steve
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[*] posted on 1-4-2006 at 01:42


Quote:
Originally posted by Flip
Is there perhaps a good way to remove the three terminal flourines? ;)
Wishful thinking probably.


are you kidding.
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Flip
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[*] posted on 1-4-2006 at 10:02


Uhhh... no. I'm really not kidding. Enlighten me.
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turd
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[*] posted on 1-4-2006 at 12:37


The C-F bond is one of the strongest bonds you will find in organic chemistry. Good luck in breaking it.

But why don't you try to make the corresponding (meth)amphetamine (try saying atfmphetamine aloud!) and characterise it? That would be interesting - more so than dull amphetamine.
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Nicodem
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[*] posted on 1-4-2006 at 12:59


Substituting the alpha-methyl group with the trifluoromethyl abolishes amphetamine-like activity in amphetamine. At least according to Pinder, Burger , J. Pharm. Sci. 56 (1967) 970. Other electron withdrawing groups, like the cyano for example, have similar effect. Only the electron donating groups (Et, allyl, ethynyl ) maintain some amphetamine-like activity in animal models.



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