Sciencemadness Discussion Board

CIS to TRANS conversion

shrent - 11-5-2006 at 08:51

Hi Dears !

I made a Cycloaliphatic Amine by reduction of its oxime. Amine received as mixture of CIS & TRANS isomers & it has been quite tedious to remove the cis isomer completely as I want only the trans amine.

Can I know about any reagents/procedure thro' which this cis amine can be converted to the trans isomer ?

Somewhere I read that some lewis acids could be used for this transformation.......but not sure.......

Pls comment......



shrent

chemoleo - 11-5-2006 at 09:54

You'll have to convert your 50% cis amine to the imine (R2C=NH), and reduce this to get the racemic mix. From this you can isolate the trans variety. So your total yields will go up incrementally... 50%, 75%, 87.5 etc etc

shrent - 11-5-2006 at 21:03

Thanks a lot for the suggetion, dear !

But can you please explain this experimentally in detail ? Otherwise any exp. reference for this ?