Consider 5-cyano-2,2-dimethylpentyl 4-methylbenzene-1-sulfonate:

5-cyano-2,2-dimethylpentyl 4-methylbenzene-1-sulfonate

What would it yield by a Lemieux-Johonson oxydation ($\ce{OsO4}$, $\ce{NaIO4}$)?

My first guess would have been that $\ce{OsO4}$ was likely to attack any of the bonds in the cycle (since they are delocalized); but would it stop here, or attack the remaining bonds? Or would something even different happen?

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    $\begingroup$ I doubt that it will attack the benzene ring in the same way that it attacks an alkene. The two do not behave much like each other as I'm sure you know. $\endgroup$ – bon Jul 15 '15 at 16:27
  • $\begingroup$ Yeah, probably nothing would happen. $\endgroup$ – Mithoron Jul 15 '15 at 16:59
  • $\begingroup$ @Mithoron Something does happen though. I'll try to find the molecules that were given after and update my question. $\endgroup$ – Hippalectryon Jul 15 '15 at 18:56
  • $\begingroup$ Can you oxidize the nitrile? $\endgroup$ – Zhe Dec 8 '16 at 23:27
  • $\begingroup$ SciFinder gives zero hits for the compound. It also does not know any reactions from compounds found by ‘substructure search’ and $\ce{OsO4}$. However, if I had to guess something would happen to the nitrile (the only remotely non-inert functional group) since nucleophilic substitutions are not possible. Oh yeah, the Kürti-Czakó is also not helpful. $\endgroup$ – Jan Dec 8 '16 at 23:27

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