ORGLIST: Aromatic substitution polymerization rxn

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From: James Giammarco (drexchem2008$##$
Date: Mon Oct 27 2008 - 15:20:14 EDT

Hi all,
       If I may, I would like to pick your brains about a general organic
chemistry problem. First, I have a reaction of para dichloro benzene with
sodium sulfide (Na2S). One can remove the Cl- and then have Na2S attack the
benzene ring. You get NaCl and you have a sulfur bridge between the benzene
rings (there are papers on this). My question is: can the same reaction be
done with sodium oxide (Na2O)? Now, I know that Na2O reacts readily with
H2O to produce NaOH but -OH, is a strong nucleophile and I think Na2O is as
well and should form the ether bridge to make poly(p-phenyl ether). It is
just I can't find any literature on it anywhere so I am wondering if I am
off track about this or if it is just so simple that it hasn't been looked
into at all. For argument sake let's say you use NMP as the solvent. Would
really like some help. Thanks!


James M Giammarco
Clemson University Graduate Student
Sirrine 060
Office: 864-656-0888

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