Author Topic: Clarke-Eschweiler reaction  (Read 6191 times)

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PEYOTE

  • Guest
Clarke-Eschweiler reaction
« on: June 18, 2000, 10:27:00 PM »
To obtain N,N-dimethyl alkanes form R-NH2, you can use the reaction of Clarke-Eschweiler
using HCOOH and CH2O in polymeric form....


Rhodium

  • Guest
Re: Clarke-Eschweiler reaction
« Reply #1 on: June 18, 2000, 10:33:00 PM »
This won't work with tryptamine. Formaldehyde and acid will lead to a pictet-spengler cyclization, forming a beta-carboline.

http://rhodium.lycaeum.org


Lilienthal

  • Guest
Re: Clarke-Eschweiler reaction
« Reply #2 on: June 18, 2000, 10:35:00 PM »
But not for tryptamines, since they will cyclize to beta-carbolines under this conditions (Pictet-Spengler reaction)  :( .


PEYOTE

  • Guest
Re: Clarke-Eschweiler reaction
« Reply #3 on: June 18, 2000, 10:51:00 PM »
I'd like to know more of this cyclization..... thanks...


Rhodium

  • Guest
Re: Clarke-Eschweiler reaction
« Reply #4 on: June 19, 2000, 12:08:00 AM »
Like this,

http://home.ici.net/~hfevans/reactions/RXN300.htm

but instead the new carbon-carbon bond is formed between the formaldehyde imine and the 2-position of the indole nucleus.