myristicinaldehyde
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Nitrostyrene -> Imine -> Ketone
2 Questions:
1. What is the name of the nitroalkane addition to an aldehyde reaction? Is it a Henry, Nitroadol, or Knoenvagel reaction? What is the difference? (It
seems the confusion from the drug forums has spread!)
2. Would reducing the nitostyrene with zinc or iron in ethanoic acid to a a,b-unsaturated amine arrange into a ketone via imine? I remember seeing
that somewhere on the forum.
- hydrogen goes over to neighboring double bond, forming a saturated imine
- imine reacts
- ????
- ketone
If this is "valid", it should be a very interesting route to phenolic ketones
I am looking to see what fun things I can make from a vanillin-nitroethane condensation product. I didnt make it yet, though!
Thanks for the help!
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Metacelsus
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1) Answer: all of the above
The Henry reaction is just another name for the nitroaldol reaction: https://en.wikipedia.org/wiki/Nitroaldol_reaction
The Knoenvagel reaction is a more general term, and includes substrates other than nitroalkanes: https://en.wikipedia.org/wiki/Knoevenagel_condensation
2) In those conditions, probably yes. The acid would promote conversion of the imine to the ketone. Under other conditions (like catalytic
hydrogenation), the amine will be formed.
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myristicinaldehyde
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Thanks!
Out of curiosity, what if I add a stearically hindering group like a tert-butyl to the imine? Would it hydrolyze to form the corresponding amine as
normal, or would the reaction fail to take place?
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