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Extraction with Acetone Options
 
Hailstorm
#41 Posted : 12/16/2020 7:58:17 AM

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xdragon wrote:
With acetone being bulkier than formaldehyde, imine formation and cyclisation rate will definitely be slower.

Acetone and DMT will not form N-isopropylidene-DMT, and Pictet-Spengler cyclization will not take place. DMT is a tertiary amine, it lacks the N-H bond that would allow the ketimine to form through a carbinolamine intermediate.
 

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downwardsfromzero
#42 Posted : 12/16/2020 3:13:22 PM

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Hailstorm wrote:
xdragon wrote:
With acetone being bulkier than formaldehyde, imine formation and cyclisation rate will definitely be slower.

Acetone and DMT will not form N-isopropylidene-DMT, and Pictet-Spengler cyclization will not take place. DMT is a tertiary amine, it lacks the N-H bond that would allow the ketimine to form through a carbinolamine intermediate.

Yes, although both NMT and tryptamine itself will form N-isopropylidene derivatives.

xdragon - inductive effects from the two methyl groups will also make the carbocation-equivalent centre less electrophilic so it's not just steric considerations that will be affecting the reaction rate.
Ora, lege, lege, lege, relege et labora

“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
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