Oxidative cleavage of 1,2-diols to give aldehydes/ketones

by James

Description: Treatment of vicinal diols (1,2-diols) with an oxidant such as NaIO4, HIO4, or Pb(OAc)4 cleaves C–C bonds and forms carbonyl compounds.
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{ 9 comments… read them below or add one }

Crystal May 28, 2012 at 6:51 am

My question is regarding Lead(IV) acetate. Does the initial compound have to have both a secondary and tertiary alcohol in order to have the reaction or can the reaction occur in the presence of just a tertiary or a secondary alcohol? In other words, could the reaction occur if the initial compound was a simple alkane with a secondary alcohol attached? Thank you! Your website and resources are fantastic and very helpful :D


james May 28, 2012 at 11:07 pm

Hi Crystal – you absolutely need two adjacent alcohols. It won’t work with a single isolated alcohol. Hope this helps – James


rishabh June 17, 2012 at 1:06 am

can we have 2 alcohols on same carbon…. ???


james June 19, 2012 at 11:36 am

Yes, it’s called a “geminal diol”, or sometimes, a “hydrate”. It will not undergo oxidative cleavage however


Anjala Wijayanthi July 19, 2012 at 4:26 am

I was struggled do my uni organic synthesis tutorial . this helped me a lot. thanks


J September 15, 2012 at 12:07 am

I have was just wondering if compounds, other than lead (IV) acetate, could be used in this oxidative cleavage? Such as Tin (IV) acetate or other acetate salts like ferric acetate or cupric acetate?


james September 16, 2012 at 6:24 pm

Sodium periodate will do it, as will periodic acid. Ruthenium tetraoxide will do this too. Tin acetate is not an oxidant; copper acetate won’t do it; Iron acetate will not lead to this oxidation in the absence of other oxidants. One could maybe add hydrogen peroxide to the Fe(III), but then all hell would break loose.


matt March 18, 2013 at 1:42 pm

when does it become a ketone and when does it become an aldehyde


james March 19, 2013 at 10:16 am

Tertiary alcohols become ketones; secondary alcohols become aldehydes; primary alcohols break off and become formaldehyde (which likely will be oxidized to CO2 under the reaction conditions)


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