Re: ORGLIST: azomethine

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From: Antonello Mai and Gianluca Sbardella (r.ragno$##$caspur.it)
Date: Tue Jul 21 1998 - 02:22:45 EDT


 On Mon, 20 Jul 1998,
barnabas liau wrote:

> Hi everybody,
> Can anyone please clear my doubt if the >C=N- system can withstand the
> basic condition namely,
> 1)NaOH (aq)
> 2)potassium tertiary butoxide (under non-aqueous condition)
> Looking forward to getting some advice.Thanks in advance.
>
> Regards,
> Barnabas
>

Dear Barnabas,
I synthesized many imines (or azomethines) and only a few of them were
stable to acqueous solution: they usually reacted with water (sometimes
even with the little moisture on the TLC plate...) to give back starting
amine and carbonyl compound (aldehyde or ketone).
I never tried to react imines with potassium tert-butoxide but I
experienced that the >C=N- system can easily react with nucleophiles (even
if the reaction goes better when acid-catalyzed).

Hope this helps,

Gianluca Sbardella


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