ORGLIST: Deprotection of a trityl group

Date view Thread view Subject view Author view Attachment view

From: Ken Knott (esprcorn$##$hotmail.com)
Date: Wed Dec 15 2004 - 23:38:50 EST


I have having issues deprotecting a trityl group from an amine. According
the the publsihed papers the deprotection should occur easily with an acidic
media. I have tried HCl, HBr, triflouroacetic acid, and others. Suffice to
say the deprotection does not occur.

I have also tried sodium in methanol based on a paper. This made a mess and
did not work.

Lastly I have tried a dehydrogenation with Pd/C catalyst 10%. This appears
to have worked though after a day at atomospheric pressure it appears to
have only been about 10-20% effective. I work in an inorganic lab and
dehydrogenation appartus is not readily available for increased pressures.
I used a baloon.

Can someone suggest possible other routes, an improved method for the
dehydrogenation, or possibly suggest a better catalyst?

Oh, and if someone can tell me why the deprotection isn't working with
acids, I am curious as everything I've seen indicaies that it should be very
facile.

Thanks,

Ken

_______________________________________________
ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net
To post a message (TO EVERYBODY) send to everybody$##$orglist.net
To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address
List coordinator: Joao Aires de Sousa (coordinator$##$orglist.net)


Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Thu Dec 16 2004 - 05:07:00 EST