From: Dr. Felix S. Sirovski (sirovsk$##$cacr.ioc.ac.ru)
Date: Thu Apr 22 1999 - 04:27:17 EDT
Dear Dr Whicker,
We had tackled this problem without much success. The most suitable
protecting group of all that we tested was tosylate. But the reaction
proceeds quite slow and product yield was about 30% (we didn't optimised
it). Perhaps under Ar or N2 blanket the yield can be higher. The presence of
CO2 leads to the multitude of side-reactions. If you have any more
questions, please send them to my home e-mail sirovski$##$gol.ru
At 11:29 20/4/99 +0900, you wrote:
>
>Dear list members,
>I am currently looking for a method to mono protect ethane-1,2-diamine
>(ethalenediamine). I wish to use the protected diamine in a double
>condensation reaction with a phenol, thus producing a six membered ring
>incorporating the 1,2 positions of the benzene ring.
>C1-O-CH2-N(CH2CH2NHP)CH2-C2.
>I believe the ether link will be susceptible to acidic
>deprotection,resulting in the reformation of the phenol.
>I an also considering the same reaction method with a hydroxyamine
>(ethanolamine etc) as such a protecting group that is also selective for
>primary alcohols over amines would be ideal.
>
>I have in mind Fmoc, as it can be removed under mild conditions, but I
>would be grateful for any input from somebody with experimental experience
>in this area.
>
>Kindly yours
>
>CW
Dr. Felix Sirovski, Ph.D., Dr.Sc., CChem, MRSC.
Head Scientist
N.D. Zelinsky Institute of Organic Chemistry of RAS
47 Leninsky pr.,
117913 Moscow
RUSSIA
Tel.: +7(095) 135-8971
Fax: +7 (095) 135-5328
E-mail: sirovsk$##$ioc.ac.ru
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