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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Lithiated on January 22, 2008, 08:01:39 PM

Title: ester cleavage with TFA
Post by: Lithiated 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!

Title: Re: ester cleavage with TFA
Post by: agrobert 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?

Title: Re: ester cleavage with TFA
Post by: Rico 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

Title: Re: ester cleavage with TFA
Post by: Lithiated 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.