Author Topic: A REALLY strange phenylethylamine synthesis!  (Read 1834 times)

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CHEM_GUY

  • Guest
A REALLY strange phenylethylamine synthesis!
« on: June 04, 2000, 09:48:00 PM »
OKay, I know that I should stop posting bizarre chemistry, but I just can't help myself.  (Probably only Rev drone and Rhodium will apreiciate this topic :) )

This is the general route to which I propose:  where Ar can be any* substituted phenyl ring
 
[ArCH2CH2CO2]2 + Cu(I)  + hv  --> ArCH2CH2CO2Cu(II) + CO2 + ArCH2CH2*

ArCH2CH2* + NH3 + Cu(II)  -{hv}-> ArCH2CH2NH2 + H(+) + Cu(I)

Here the article...

"Mechanism of Electron transfer Oxidation of
 Alkyl Radicals by Copper(II) Complexes", in The Journal of the
American Chemical Society, Vol 90, yr 1968, page 4616-4625. Also there
is another article in the same volume on  page 4038-4050, it is also a
good one.

The article use Cu(II) species to decompose peroxides (!) to alkyl
radicals that either form alkenes or nucluephilic substituted alkanes
 (!).

Page 4616
 "Oxidative elimination

>CH-C<*  -->  >C=C, + H(+) + e

Oxidative substitution

 >CH-C<*  -->  >CH-C<-N(+) + e

N = necleophile = HOAc, HOR, CH3CN, ArH, etc. ..."

Page 4618
"Kinetics of Oxidation of [Beta]-Arylethyl Radicals. [Beta]-Arylethyl
radicals (substituted on the ring) were derived from the catalyzed
decomposition of substituted hydro-cinnamoyl peroxides [1]. Oxidation
of these [Beta]-arylethyl

[ArCH2CH2CO2]2 + Cu(I) --> ArCH2CH2CO2Cu(II) + CO2 + ArCH2CH2*___(15)

radicals with Cu(II) gave a mixture of elimination
 (styrenes) and substitution ([beta]-arylethyl acetates)
products. The relative amounts of aceate and
styrene derivetives represented the relative rates of
oxidative substitution, Ks, and elimination, Ke, respectively. ...

 ArCH2CH2* + HOAc + Cu(II) -{Ks}-> ArCH2CH2OAc + H(+) + Cu(I)___(16)

ArCH2CH2* + Cu(II) -{Ke}-> ArCH=CH2 + H(+) + Cu(I)___(17)"

------------------------------------------
Hopefully I didn't include any mistakes, typos or whatnots....

This post is for informational purposes only an is not intended to facilitate illegal activity.

CHEM_GUY

  • Guest
hello
« Reply #1 on: June 07, 2000, 03:02:00 PM »
Is this a strange synthesis or what?  I see noone has jumped on this topic.  It seems like a good synthesis from cinnamon phenyl derivatives.  Maybe some day some one some where will find this interesting as I have...

This post is for informational purposes only an is not intended to facilitate illegal activity.

WizardX

  • Guest
Re: hello
« Reply #2 on: June 08, 2000, 05:58:00 AM »
Chem_Guy: "I see noone has jumped on this topic?"


This only is for Rev drone and Rhodium


I see you haven't invited anyone else.




CHEM_GUY

  • Guest
Re: hello
« Reply #3 on: June 08, 2000, 02:04:00 PM »
Holy shit I didn't even notice that!  I meant to put a "probably" in there, with the proper syntax of course.  My apologes.

I here by humblly invite all to this topic.  I do not know if this will work but it seems likely...

This post is for informational purposes only an is not intended to facilitate illegal activity.

CHEM_GUY

  • Guest
Re: A REALLY strange phenylethylamine synthesis!
« Reply #4 on: June 23, 2000, 11:16:00 AM »
Does anyone know how to create a cinnimoyl peroxide?  [Ar-CH2CH2-CO2]2

This post is for informational purposes only an is not intended to facilitate illegal activity.

wayupnorth

  • Guest
Re: A REALLY strange phenylethylamine synthesis!
« Reply #5 on: July 25, 2000, 10:08:00 PM »
I just receive 7000-ml of 2-phenylethylamine and its C6H5CH2CH2N2, maybe N3, Damn wish I had done more than a minor in organic chem.  I was gonna monomethylate at the amine, but what to do at the top.  Hey, wish it was so strange as I got this reagent stuff and......  It as 2-phenylethylamine sure looks alway different for the same name.


PVnRT_NC8

  • Guest
Re: A REALLY strange phenylethylamine synthesis!
« Reply #6 on: July 26, 2000, 12:29:00 AM »
I aint shure but I belive pine trees and such are full of stuff like ciniminoyl, distill a XMASTREE yet?

CAn you belive all the crap and how fact a tiny cattipiliar eats I cant, this one tiny catipliaiar eats six or seven morning glory leaflets a day...

A010

wayupnorth

  • Guest
Re: A REALLY strange phenylethylamine synthesis!
« Reply #7 on: July 27, 2000, 11:56:00 PM »
Does me little good.  I'm starting with your finished project, the petrochemical refinery labs use shit loads of it.  As well as any university with a petroleum engineering department.   Monomethylation at the amine is easy, as long as you use paraformaldehyde instead of formaldehyde, but hum, any suggestions on an easy addition method for  carbolation back up top.

wayupnorth, yep, yep, yeppar and a blah sa, blah sa, blah.

Whizard

  • Guest
Re: A REALLY strange phenylethylamine synthesis!
« Reply #8 on: August 22, 2001, 10:43:00 AM »
Never stop posting this kind of stuff! The most facile reactions are often the most obsure. It is these kind of tidbits that make trying to stop us im-fucking-possible!

I dunno, but I been told ... You never slow down, you never grow old!

zed

  • Guest
Reaction path.
« Reply #9 on: April 26, 2002, 11:32:00 PM »
upnorth, the reaction path you wish to follow is not known to us.

I assume your "up top" reference, refers to methylating the alpha carbon of your B-phenyl-ethylamine. Thus, producing amphetamine. Sorry, not easy. Still, chemistry does change, and it may be more feasable someday.

To "stabilize" your reagent until such a day comes, I suggest you either return it to where you got it, or place it in an ammo-box, wrap it in plastic and bury it deep.

If a DEA agent should come across this material, and find you also have some drug chemistry paperwork around; It will make a profoundly negative impression.

It isn't very useful for your desired purpose, but it is quite useful in some reactions that really, really, piss the government off.

Live long and prosper!........Your Friend, zed