Oxalyl chloride

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vidavsky@gmail.com - 03 Oct 2005 09:48 GMT

Hi,

I have a little problem to find the mechanism for the reaction of
Oxalyl chloride and carboxylic acid.

If you can tell about a good web site it will be nice.

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stephan.j.bird@mad.scientist.com - 05 Oct 2005 08:54 GMT

> Hi,
>
> I have a little problem to find the mechanism for the reaction of
> Oxalyl chloride and carboxylic acid.
>
> If you can tell about a good web site it will be nice.

Not sure about a web site per se, but how does attack of the
hydroxyl group (or the anion, pH dependent) to one of the
carbonyls of the oxalyl chloride seem as a starter for 10.

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Stephan Bird MChem(Hons) AMRSC
Currently in Caernarfon, Wales

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Namast? - 10 Oct 2005 09:45 GMT

Greetings,

you can find the mechanism proposed for the transformation of
carboxylates into acyl chlorides in the March's textbook.
If you don't have the book, in this link you could find the mechanism
http://www.chemistry.ohio-state.edu/~lowary/H252WEB/notes/H252NOTES20.PDF
In a few words the carboxylate attacks the oxalyl chloride to carry out
a acylic nuckeofilic substitution to give an anhydride, and then the
eliminated chloride attacs the anhydride to give the acyl chloride and
CO2.

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Natural Science Forum / Chemistry / Organic Synthesis / October 2005

Oxalyl chloride