ORGLIST: knoevenagel reaction with 2,3,3-trimethyl-indolium

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From: Shenliang Wang (shenliangwang$##$
Date: Thu Mar 24 2005 - 19:30:08 EST

Hi everybody,

I am doing knoevenagel reaction with
2,3,3-trimethyl-indolium salt. However, this starting
material seems to be very wired. When it remains the
ammonium salt form, it is very reactive, while it is
very inert to reaction if treated with base to form
1,3,3-trimethyl-2-methyleneindoline(as in the attached
figure.) This leads to very low yield, no matter under
normal heating or microwave condition.

Does anyone have some personal experience with it? How
can I transform it back to the ammonium form, if
possible? Can someone suggest some better catalysts?
So far, various amines including pyrrolidine and
piperidine, ammonium acetate, sodium acetate, and
piperidium acetate have all been tested. I am really
exhausted by this problem.

Thanks a lot in advance.
Shenliang Wang

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