KingBoo
Harmless
Posts: 11
Registered: 11-5-2013
Member Is Offline
Mood: No Mood
|
|
Adamantane Synthesis Mechanism
http://upload.wikimedia.org/wikipedia/commons/4/4d/Adamantan...
Can someone please explain the mechanism of the last step? Thanks!
|
|
|
ThePorkWhisperer
Harmless
Posts: 2
Registered: 23-8-2013
Member Is Offline
Mood: No Mood
|
|
the best I can come up with is Friedel Crafts, where the right-hand side's C-C bond is broken, leading to a ring annulation
...or am I completely off?
|
|
|
smaerd
International Hazard
Posts: 1262
Registered: 23-1-2010
Member Is Offline
Mood: hmm...
|
|
Don't see how it is ring annulation (no enolate possible), or friedel crafts (no aromatic ring or alkyl/acyl halide).
It is a rearrangement of some kind. Doing some quick research on it I found it is called an 'adamantane rearrangement'. Exactly how it works I am not
sure but I sort of have an idea.
Here's a review article that appears to have information about it -
http://pubs.rsc.org/en/content/articlelanding/1974/cs/cs9740...
Adamantane rearrangements
M. Anthony McKervey
Chem. Soc. Rev., 1974,3, 479-512
DOI: 10.1039/CS9740300479
If I had access I would look into it.
|
|
|
Dany
Hazard to Others
Posts: 482
Registered: 3-8-2013
Member Is Offline
Mood: No Mood
|
|
Some interesting papers on adamantan rearrangement.
Dany.
Attachment: Adamantane rearrangement mechanisms. 1,2-trimethylenenorbornanes.pdf (210kB)
This file has been downloaded 927 times
Attachment: Adamantane rearrangements.pdf (1.9MB)
This file has been downloaded 3095 times
Attachment: On the mechanism of adamantane rearrangements.pdf (364kB)
This file has been downloaded 886 times
|
|
|
KingBoo
Harmless
Posts: 11
Registered: 11-5-2013
Member Is Offline
Mood: No Mood
|
|
Thank you very much Dany 
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
