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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, 2015 at 16:27
  • $\begingroup$ Yeah, probably nothing would happen. $\endgroup$
    – Mithoron
    Jul 15, 2015 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, 2015 at 18:56
  • $\begingroup$ Can you oxidize the nitrile? $\endgroup$
    – Zhe
    Dec 8, 2016 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, 2016 at 23:27

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