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I was wondering if substituted pyridines can work the way pyridine does in order to oxidize alcohols to aldehydes. Of course, I'm referring to pyridines without any functional group which can undergo oxidation reactions (eg: I was thinking methylpyridine, or trimethylpyridine, with the nitrogen untouched.)

I guess that the reactivity is the same, but is there any reference to the use of this kind of reagent?

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    $\begingroup$ I think the main role of pyridine is to abstract the chloride ion from the intermediate formed leading to an elimination reaction. So yeah, the substituted ones should also work. However, its efficiency might be reduced as the +I effect of the substituents will decrease the net positive charge on nitrogen in pyridine. $\endgroup$ Apr 15, 2017 at 11:28

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Collidinium chlorochromate and gamma-picolinium chlorochromate are known oxidising agents. e.g. Synth Comm. 31 2001 1253

I see no reason why other methyl pyridines should not also work.

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  • $\begingroup$ There may be steric issues with bulky primary alcohols. $\endgroup$
    – Zhe
    Apr 15, 2017 at 15:28
  • $\begingroup$ Triggered by the two chemical names mentioned, I found it interesting to browse before and after this page google books provides: books.google.de/… $\endgroup$
    – Buttonwood
    Apr 15, 2017 at 21:38

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