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What mechanism causes nitroalcohol dehydration following the henry reaction?

Brainfarction  Follow
I ran into some readings that seemed to imply that dehydration is favored at low temperatures in some cases if the hydroxyl group is close to an unreduced aromatic ring because the electron withdrawing properties of the double bonds. Though, all references to this that I have found have been vague at best

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Davis Sedick  Follow
I don't think so. Many of the particular reactions occur in base only environments. I've noticed the trend in that high levels of base = dehydration, and low levels of base = reduced amounts of dehydration.

There are particular cases were sodium bisulfate is used with the aldehyde to create an abduct that is not subject to dehydration but will still undergo condensation

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David Dowler  Follow
I've wondered this too, I always assumed you needed a proton source in the reaction mixture to dehydrate to the nitroalkene

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Dario Cansino  Follow
Am I allowed to *Ignore me, I am impatient* this?

I've noticed some particular molecules seem to automatically dehydrate, while others don't. Though this doesn't make very much sense seeing as the merging of the aldehyde and the nitroalkane is pretty standard on most substrates in this type of reaction. What conditions facilitate dehydration of the molecule? I first thought temperature might be the culprit, but further looking at various papers on the topic, some reactions are run at low temperatures(below freezing) others at high temperatures (above 80c), yet yield dehydrated products.

Anyone have a clue?

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