From: Eugene Leitl (eugene.leitl$##$lrz.uni-muenchen.de)
Date: Fri Jun 25 1999 - 14:27:30 EDT
Jim Sims writes:
> There are a number of dissolving metal reductions that will reduce
> aldehydes. One may work for you . Sodium in alcohol; Sodium, Potassium or
> Lithium in Ammonia; Iron in acetic acid and water; Zinc Mercury amalgam in
> HCl and water. JIM
Thank you. I'd rather avoid any pH extremes since they visibly damage
the polymer. I tried the aluminum amalgam reduction yesterday -- with
somewhat messy and baffling results. The deep cherry red coloration I
observed with sodium borohydride reduction also appeared (but much
weaker) with AlHg, mostly spotting the surface of the amalgam. (It
obviously cannot be a metal complex, what on earth is that, then?)
At this point I think I'd rather try the Mg/CuCl2 procedure kindly
suggested by Dr Jost T Bohlen <bohlen$##$fiz-chemie.de> (SARANGI, C.;
NAYAK, A.; NANDA, B.; DAS, N. B.; SHARMA, R. P.; Tetrahedron Lett
[TELEAY] 1995, 36 (39), 7119-7122.), perhaps trying vanilla
Meerwein-Pondorff-Verley before.
The Raney Ni procedure seems to work, but the filtration process to
get rid of the metal/hydride sludge is too slow. Perhaps I should
try centrifugation before filtration.
Since no private replies were forthcoming so far there is no need for
a summary.
Thanks to everybody who responded.
Regards,
Eugene Leitl
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