Recently I was having some fun by reading http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0542 (http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0542)
, linked from https://www.thevespiary.org/rhodium/Rhodium/chemistry/pyrrolidinyl.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/pyrrolidinyl.html)
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I you scroll down to the discussion and have a look at the table you will see a number of examples were benzaldehydes and a benzyl bromide are reacted with various lithiated nitrosamines, yielding, in the case of the benzaldehydes, N-substituted alpha-hydroxyphenethylamines and, of benzyl bromide a N-substituted phenethylamine.
One of the most interesting reactions is where benzaldehyde is reacted with the lithiated nitroso-diethylamine, to give n-ethyl ephedrine.
Well, it looks to me that if one were to use benzyl bromide or piperonyl bromide in that reaction the product would be the n-ethylamphetamine.
Now, What I want to ask you people is: what if methylethylamine is used? Will the lithium atom attatch itself to the methyl or to the alpha carbon of the ethyl chain.
I guess you can see where I am getting at.