Sunlight, thank you for all the great references, I will study them carefully. To this point, I haven't found a reference, to anyone doing what both of us considered to
be possible....decarboxylating to the methylimine, followed by reduction to amine. Quite correctly, you stated that most
experiments produce nothing. I spent years conducting experiments that usually ended that way; In O Chem. experimental results trump theory most of the time. To my
great pleasure, occasionally I have dreamt a reaction sequence that worked really well! I will puzzle over this problem and contact you if a light clicks on. In the meanwhile, I will continue to be of the opinion that, for the present, in-situ reduction of nitromethane to
methylamine by disolving metal reduction, or hydrogenation..
may be the most effective way to aminate Phenylisopropanones.
Nitromethane is easily acquired, but not good to have around
the lab, as it seems to create suspicion with law enforcement agents: A problem many of the Bees are concerned with. A wise solution to this problem, is to store
such reagents underground, in a remote location. Ammo boxes
work very well for such storage. They are hermetically sealed, and if well wrapped in plastic, and buried, they
provide safe dry storage for many years. Large diameter ABS tubing (Soil or Drain pipe)also provides excellent storage.
A foot long section, with screw caps glued on it's ends, makes a very strong, waterproof, storage container. A post hole digger can quickly make a hole two feet deep. Just slip the cylinder in, and bury it. Thereafter, sleep soundly at night. This is not to suggest doing anything illegal. It is simply that a person of refinement, should at all times, avoid the appearance of impropriety.
Being a bee is something, most people rapidly grow out of.
It is best that they grow out of it naturally. Not, because
some terrible legal misunderstanding, leads to incarceration.
Oh, we didn't discuss the possibilty of reducing the amino-
acid imine, before decarboxylation. Then heating the product
to decarboxylate. I don't know if an N-Substituted aminoacid
can be decarboxylated. Do you? Oh, I know microbes can do it, but they can do anything. Every living cell on earth has 2.5 Billion years of O-Chem backround.
Decarboxylation after reduction seems less elegant, than the
initial approach. But, what the heck, it could be O.K......
If my glassware wasn't in another time zone, I would try it
right now.
Thanks again for your input...........Zed