Imides,tertiary amines

[Phil Young]

I am trying to break an imide bond.

O
\\
R - C
\
N--R -O - R
/
R - C
//
O

So far I think i can attack it with a Strong Lewis base.

Anyone have any suggestions?

Phil....@engineers.com

[Alan "Uncle Al" Schwartz]

phil....@engineers.com (Phil Young) wrote:
> I am trying to break an imide bond.
>
> O
> \\
> R - C
> \
> N--R -O - R
> /
> R - C
> //
> O
>
> So far I think i can attack it with a Strong Lewis base.

You need something aggressively nucleophilic and sterically undemanding.
Dicyclohexano-18-crown-6 complexed KOH in toluene, or crown-complexed
KO2 (superoxide) in DMSO followed by sulfite reduction, or KOH
concentrated aqueous plus 10 mole-% imidazole and maybe a percent of
4-dimethylaminopyridine. Basic hydrogen peroxide followed by a sulfite
reduction might be cute. Methylhydrazine plus KOH should also work.

Or cook it to death in HCl (conc.).

If you use a phthaloyl protecting group next time, crack it with
methylhdyrazine, which is very facile indeed (See Fieser and Fieser).

--
Alan "Uncle Al" Schwartz
Uncl...@ix.netcom.com ("zero" before @)
http://www.ultra.net.au/~wisby/uncleal.htm
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