joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
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Mood: what is mood?
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nitroalkenes, nitronates, reduction of these, nef reaction
i would like to hear suggestions and opinions about the following reaction scheme:
lets say we have a mixture of a water insoluble polymer and a secondary nitroalkene. to separate the two, the mixture is treated with potassium
hydroxide solution to form the water soluble nitronate salt. does this happen at all, since the neighboring double bond inhibits the needed C-H
acidity?
if it is possible, will throwing some NaBH4 in the same solution reduce the double bond and allow for a subsequent Nef reaction to yield a ketone?
stupid questions all in all since the first step most likely doesn't work at all, i've previously treated nitroalkenes with base and
well...it got blue or red. but maybe someone can clear things up a bit, not too difficult to figure out what i'm heading for, right? 
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Sandmeyer
National Hazard
Posts: 784
Registered: 9-1-2005
Location: Internet
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Mood: abbastanza bene
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You can't do that, nitrostyrene is a michael acceptor, hydroxide ion will add and not deprotonate, deprotonation is possible only with
nitroalkanes. wash the nitrostyrene with cold IPA under suction and do a recrystalization to remove the polymer.
[Edited on 17-9-2005 by Sandmeyer]
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