Thiyl Radical Mediated Racemization of Non Activated Aliphatic Amines

sharetea

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Some background

Data reported to the European Commission indicates that in 2020, 327 kilograms of AIBN, 525 kilograms of methyl thioglycolate, 248 kilograms of dimyristyl peroxydicarbonate and 2.5 litres of thioglycolic acid were seized in Europe.



General procedure for the racemization experiments:
A 0.06M solution of amine (100 mg) and
thiol (1.2 equiv or 0.2 equiv) in benzene was refluxed for 2 h (stoichiometric condition) or 7 h (catalytic
condition) in the presence of AIBN (whenever the reaction time was superior to 2 h, the overall quantity
of 20 mol% of AIBN, was divided in three equal portions that were added successively each 2 hours).
After concentration, the residue was diluted with HCl (1M) and the solution was washed with Et2O. The
aqueous phase was basified with saturated sodium carbonate and extracted with Et2O. The pure amine
was isolated after drying on MgSO4 and concentration.


I havent wrapped my head around it yet.. If som1 does can they explain why 4 ingredients siezed.. Are two substitues.. ?? I guess i need to put up pictures of the structures..

Documents and refernced linked..
 

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sharetea

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Thio
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Thioglycolic acid​

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Methyl thioglycolate​


Dimyristyl peroxydicarbonate i guess this is a super special base for the s to atach to oxygenate..i need to study some more​

8HixFOVWwk
 

sharetea

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Hmmm looks like the funnny long looks like only aibn is common intiator and evey other ingredient is its own method.

Thats my pelminary research..you can get aibn from wendylucky havent earched for thioyly yet..

All the info to turn l-meth into l/d-meth.. The missing step
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btcboss2022

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I think I found an interesting easier way to test.
To 1M of freebase of the undesired isomer add 0.2 eq of anhydrous AlCl3 or FeCl3 and reflux at 150C during 10hours.
I need to find some time to test it correctly but seems easy if anyone could do it please..
Thanks.
 
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