Photo-induced nuclephilic amination

[N3XU5]

So I read about amination of nitrostyrenes using ammonia gas recently that involved skipping reductive amination with the use of sodium*boro*hydride by utilizing a high-pressure mercury vapor lamp under cooling.

"General procedure of Photoamination. Into a Pyrex vessel was introduced an MeCN-H2O (9:1, 70 mL) solution containing 1-4, 6-8 [various styrenes] (3.5 mmol) and DCB (3.5 mmol), and then the solution was bubbled with gaseous ammonia. The solution was irradiated by an eikosha PIH-300 high pressure mercury vapor lamp under cooling with water. The progress of the reaction was followed by GLC analysis..."
Neunteufel, R. A., Journal of the American Chemical Society, 1973, 95, 4080-4081

Anyone know the yields on this particular method? Supposing it's viable one could go from iso--->product (replacing ammonia with methylamine). One pot. Two step start to finish.

[cws910]

Here's an article on the photoamination of isosafrole (all in pursuit of MDMA) The anaologous non-benzodioxole compound could be used ( 2-prop-1-enyl benzene, which could be prepared by isomerization from 2-propenylbenzene)

https://www.erowid.org/archive/rhodi...amination.html

Enjoy,

-C

[Average Fuckin Joe]

Originally Posted by N3XU5

So I read about amination of nitrostyrenes using ammonia gas recently that involved skipping reductive amination with the use of sodium*boro*hydride by utilizing a high-pressure mercury vapor lamp under cooling.

"General procedure of Photoamination. Into a Pyrex vessel was introduced an MeCN-H2O (9:1, 70 mL) solution containing 1-4, 6-8 [various styrenes] (3.5 mmol) and DCB (3.5 mmol), and then the solution was bubbled with gaseous ammonia. The solution was irradiated by an eikosha PIH-300 high pressure mercury vapor lamp under cooling with water. The progress of the reaction was followed by GLC analysis..."
Neunteufel, R. A., Journal of the American Chemical Society, 1973, 95, 4080-4081

Anyone know the yields on this particular method? Supposing it's viable one could go from iso--->product (replacing ammonia with methylamine). One pot. Two step start to finish.

The only thing I understood out of this whole shit was.... Neunteufel.

Meaning, 9 Demons.

lol