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Natural Science Forum / Chemistry / Organic Synthesis / June 2005



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POCl3 + alkene = ?

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Dimonatorr - 26 May 2005 08:24 GMT
Hello, all!

Could anyone help me to find an answer to the following question: what
are the products of the interaction between POCl3 and an alkene? What
is a mechanism of this reaction?

Thanks in advance,
Dmitry.
Gabriel Tojo - 06 Jun 2005 11:21 GMT
> Hello, all!
>
> Could anyone help me to find an answer to the following question: what
> are the products of the interaction between POCl3 and an alkene? What
> is a mechanism of this reaction?

The quick answer is "no reaction."

An alkene with an average alkene reactivity bellow ca.200 ?C will not
react with POCl3 ?with no help of catalysis? to any appreciable extent.

I suppose that given enough temperature or under the help of some
catalysis something will happen, and we could expeculate about the
result for long, but, as long as I know, this is not part of the
standard synthetic techniques.

Some adventitious water could react with POCl3 resulting in HCl that
could add to some alkenes producing alkyl chlorides.

Best regards.

Gabriel Tojo
 
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