[endophytic]

Hello all !

I'd like to form an hydroxamate from methyl ester on a molecule containing a γ-lactone. Will the lactone be aminolysed ? Is it avoidable ?



The hydroxamate reaction I want




The side reaction I don't want !

Will this happen ?
At room temp ?
Is there a way to avoid it ?


Thanks all 

[orgopete]

Try it!

I would expect different substrates to have different rates, therefore some selectivity seems reasonable. A lower temp would improve selectivity, but also slow the rate. Will an alpha amido group slow the rate enough? You know what to do.

[endophytic]

Thanks orgopete

I read this article http://pubs.acs.org/doi/abs/10.1021/ja00436a022
And it's a bit of chinese to me ... 
From what I got  aminolysis of δ-lactone is more comparable to  that of phenyl acetate and activated esters than straight chain alkyl esters. Does this means that in my case case lactone opening should be favorised over hydroxamate formation ?

What would the alpha amido group influence supposed to be ?

Anyway i'll try ...

Thanks !

[orgopete]

I agree that I would expect a simple lactone to react faster, however the amido group should also slow reaction. What will be the final result? I don't know. If you had one mole of lactone, ester, and hydroxylamine, I would be surprised to find exactly a 50.0:50.0 mixture. I think your ester will react faster, but that is only a guess. If you try the reaction, you can tell us what happened.