Comments on: Oxidative Cleavage of Vicinal Diols With NaIO4 and Pb(OAc)4 https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/ Wed, 12 Nov 2025 20:58:45 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-772479 Thu, 18 Sep 2025 18:48:21 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-772479 In reply to Aakash.

Each of them add water to form the respective hydrates. Then the OH groups from adjacent hydrates coordinate to iodine and the oxidative cleavage proceeds from there.

]]> By: Aakash https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-772457 Thu, 18 Sep 2025 14:09:34 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-772457 What should be the mechanism in case we have 1,2 diketo groups

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-686858 Thu, 07 Mar 2024 16:52:02 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-686858 In reply to Prajwal Mallikarjun Timashetti.

No, no oxidative cleavage will occur. Both groups need to be OH so they can coordinate to iodine. If one of the oxygens is an ether, then no reaction will take place.

]]> By: Prajwal Mallikarjun Timashetti https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-686845 Thu, 07 Mar 2024 12:48:11 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-686845 actually my question was will the nai04 give same answer with ch3-o-ch2-ch2-oh?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-686747 Wed, 06 Mar 2024 15:52:14 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-686747 In reply to Prajwal Mallikarjun Timashetti.

That would not be a good solvent for an oxidant like NaIO4. I would use an inert ether solvent.

]]> By: Prajwal Mallikarjun Timashetti https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-686695 Wed, 06 Mar 2024 05:05:33 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-686695 Sir, Can you also tell me what are the conditions (pressure and temperature) at which this reaction will be taking place.

]]> By: Prajwal Mallikarjun Timashetti https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-686693 Wed, 06 Mar 2024 04:56:23 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-686693 Dear Sir, is this reaction possible in ch3-o-ch2-ch2-oh ? please help me out

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-564391 Wed, 18 Sep 2019 17:40:53 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-564391 In reply to k murali krishna.

That doesn’t make sense. You’re missing a carbon somewhere. It can’t just be NaIO4, you’re likely treating cyclohexane 1,3-dione with OsO4 first.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-563296 Thu, 05 Sep 2019 19:13:14 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-563296 In reply to Rajesh.

If the alcohols are both on equatorial positions, then it can be done.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/10/21/sodium-periodate-oxidative-cleavage/#comment-563292 Thu, 05 Sep 2019 19:09:14 +0000 https://www.masterorganicchemistry.com/?p=2517#comment-563292 In reply to Vardan.

I don’t think beta amino alcohols can be cleaved. Only alpha amino alcohols. E.g. serine. https://pubs.acs.org/doi/abs/10.1021/ja01875a521

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