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Extraction with Acetone Options
 
Hailstorm
Chemical expert
#41 Posted : 12/16/2020 7:58:17 AM
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.
 
downwardsfromzero
ModeratorChemical expert
#42 Posted : 12/16/2020 3:13:22 PM
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.




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