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Topic: Lactone to pyrane  (Read 5779 times)

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omoli062

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Lactone to pyrane
« on: April 25, 2006, 03:38:11 PM »
I have a little problem with this reaction, a have to do the synthesis of  a pyrane from a lactone , All R most be only alkyl groups ??? any idea??? ??? ???

Offline AWK

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Re: Lactone to pyrane
« Reply #1 on: April 26, 2006, 02:19:53 AM »
This is a problem, how to form C-C bond from oxygen function
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Offline Winga

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Re: Lactone to pyrane
« Reply #2 on: April 26, 2006, 04:03:34 AM »
I have a little problem with this reaction, a have to do the synthesis of  a pyrane from a lactone , All R most be only alkyl groups ??? any idea??? ??? ???
I think the 1st step is to eliminate all the -OH groups, and the major product should be conjugated one.
Then, additions of alkyl groups, e.g. 1,4 addition (not quite sure).
About the C=O group, use ylide to convert to C=CRR'.

Offline AWK

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Re: Lactone to pyrane
« Reply #3 on: April 26, 2006, 05:28:38 AM »
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About the C=O group, use ylide to convert to C=CRR'.
Does lactone carbonyl group react with ylide?
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Offline Winga

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Re: Lactone to pyrane
« Reply #4 on: April 26, 2006, 06:22:23 AM »
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About the C=O group, use ylide to convert to C=CRR'.
Does lactone carbonyl group react with ylide?
Not sure! ;D

Offline movies

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Re: Lactone to pyrane
« Reply #5 on: April 26, 2006, 11:18:11 AM »
Quote
About the C=O group, use ylide to convert to C=CRR'.
Does lactone carbonyl group react with ylide?

If by ylide you are referring to a Wittig reagent, then no, it won't react with an ester/lactone.

There are other reagents to convert an ester/lactone to an enol ether though, including the Tebbe reagent and the Petasis reagent.

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