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Topic: ester cleavage with TFA  (Read 8985 times)

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Offline Lithiated

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ester cleavage with TFA
« on: January 22, 2008, 08:01:39 PM »
Dear all, does anyone know the mechanism for the tert-butyl ester cleavage
using TFA in dichloromethane? I can't locate it anywhere,
Thanks,

Lithiated!
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Offline agrobert

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Re: ester cleavage with TFA
« Reply #1 on: January 22, 2008, 08:35:18 PM »
What is TFA? What do acids do to esters? Which oxygen is protonated first?  What is the geometry of a  hemiacetal?
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In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline Rico

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Re: ester cleavage with TFA
« Reply #2 on: January 23, 2008, 10:15:51 AM »
Hey Lithiated

If it is the mechanism of the removal of a BOC-group, from for instance a protected amino-group, you are looking for, i've attached it in a jpeg file.

I hope this is what you are looking for

Rico

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Offline Lithiated

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Re: ester cleavage with TFA
« Reply #3 on: January 24, 2008, 02:12:38 AM »
Dear Rico, thanks for your help. i think you're right. The first step might also
be attack on H+, depending on the ionization of CF3COOH in CH2Cl2 ?

Cheers,
Lithiated.

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