KingBoo - 23-8-2013 at 10:15
http://upload.wikimedia.org/wikipedia/commons/4/4d/Adamantan...
Can someone please explain the mechanism of the last step? Thanks!
ThePorkWhisperer - 23-8-2013 at 12:16
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 - 24-8-2013 at 08:12
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 - 24-8-2013 at 16:27
Some interesting papers on adamantan rearrangement.
Dany.
Attachment: Adamantane rearrangement mechanisms. 1,2-trimethylenenorbornanes.pdf (210kB)
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Attachment: Adamantane rearrangements.pdf (1.9MB)
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Attachment: On the mechanism of adamantane rearrangements.pdf (364kB)
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KingBoo - 24-8-2013 at 19:01
Thank you very much Dany 