Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: protection of one of the two ketone sites
chemrox
International Hazard
*****




Posts: 2961
Registered: 18-1-2007
Location: UTM
Member Is Offline

Mood: LaGrangian

[*] posted on 1-11-2012 at 20:56
protection of one of the two ketone sites


Piperidione, 3,3-diethylpiperidine-2,4-dione, CAS 77-03-2, has two oxo groups. The molecule is almost bilaterally symmetrical, but not quite. One of the two oxo's is adjacent to a piperidyl N. What I would like to do is perform reductive ams with different amines on both oxos or a reductive am on one and maybe a Grignard to the other. Anyway, in order to be able to treat these separately it will be necessary to protect one of the oxos. I'm asking if this is feasible and whether the placement of one of them adjacent to the secondary amine helps make this possible?



"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
View user's profile View All Posts By User
DJF90
International Hazard
*****




Posts: 2266
Registered: 15-12-2007
Location: At the bench
Member Is Offline

Mood: No Mood

[*] posted on 1-11-2012 at 21:31


The carbonyl in the 2-position is part of the amide functionality. As such it will be much less reactive towards nucleophiles than the 4-one.
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
2-11-2012 at 04:22

  Go To Top