{"id":2517,"date":"2011-10-21T22:17:09","date_gmt":"2011-10-21T22:17:09","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=2517"},"modified":"2025-11-12T14:58:45","modified_gmt":"2025-11-12T20:58:45","slug":"sodium-periodate-oxidative-cleavage","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/10\/21\/sodium-periodate-oxidative-cleavage\/","title":{"rendered":"Oxidative Cleavage of Vicinal Diols With NaIO4 and Pb(OAc)4"},"content":{"rendered":"

Sodium Periodate, NaIO4<\/sub> As A Reagent In Organic Chemistry<\/strong><\/p>\n

In a blatant plug for the\u00a0Reagent Guide <\/a>\u00a0each Friday \u00a0I profile a different reagent that is commonly encountered in Org 1\/ Org 2.\u00a0<\/em><\/p>\n

\"structure-of-sodium-periodate-naio4\"<\/a><\/p>\n

In organic chemistry, sometimes you need to build molecules up. Other times, you need to break molecules down. Ozone, which we talked about earlier<\/a>, is a really useful reagent for that. Here’s another one, although it’s a little more obscure.<\/p>\n

Sodium Periodate (NaIO4<\/sub>) Cleaves 1,2-Diols (“Vicinal” Diols) To Aldehydes And Ketones<\/h2>\n

Sodium periodate (NaIO4<\/sub>) breaks apart 1,2-diols (“vicinal” diols) to form aldehydes and ketones<\/strong>. In this respect it’s the same as periodic acid (HIO4<\/sub>) and lead tetra-acetate [Pb(OAc)4<\/sub>].<\/p>\n

\"naio4-for-cleavage-of-diols-to-give-aldehydes-and-ketones\"<\/a><\/p>\n

Notice what’s happening to NaIO4 here – it’s becoming reduced from iodine(VII) to iodine(V). In the process we’re cleaving a C-C bond and forming two C-O\u00a0\u03c0 bonds. Comes in handy sometimes, when you want to break apart an alkene and form aldehydes and ketones.<\/p>\n

Cleavage Of Vicinal Diols By Sodium Periodate (NaIO4<\/sub>) \u2013 \u00a0The Mechanism<\/strong><\/h2>\n

The first step in cleavage of vicinal diols by NaIO4<\/sub> is the direct attachment of the alcohols to the iodine. This occurs through two successive attacks of the iodine by lone pairs on each of the hydroxyl groups followed by a proton transfer.<\/p>\n

In the second step, what happens is a kind of reverse cycloaddition (similar to what happens when an ozonide breaks down). This is a somewhat simplified version of the mechanism (skipping over the proton transfer). The key part here is the third diagram, where the cyclic iodate ester breaks down to give the ketone and aldehyde.<\/p>\n

\"mechanism-of-naio4-cleavage-of-diols-to-give-carbonyl-compounds\"<\/a><\/p>\n

And there you go: aldehydes or ketones, depending on whether you’re breaking down secondary or tertiary alcohols (primary alcohols become formaldehyde). So this actually gives you a second way<\/em> to cleave double bonds to alkenes\/ketones besides ozone. You can take an alkene, treat it with osmium tetroxide<\/a> (OsO4<\/sub>) first to make the diol, and then NaIO4<\/sub> it. This is, incidentally, sometimes called “Johnson-Lemieux cleavage<\/a>“. Obscure organic chemistry named reaction of the day!<\/p>\n

P.S. You can read about the chemistry of NaIO4<\/sub> and more than 80 other reagents in undergraduate organic chemistry in the “Organic Chemistry Reagent Guide”,\u00a0available here as a downloadable PDF<\/a><\/em>.<\/a><\/p>\n

\n

<\/a>Quiz Yourself!<\/h2>\n\n

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Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n

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\n

(Advanced) References and Further Reading<\/strong><\/p>\n

The most common oxidizing agents used for this reaction are KMnO4<\/sub>, periodic acid (Malaprade reaction), and Pb(OAc)4 <\/sub>(Criegee reaction).<\/p>\n

    \n
  1. Malaprade, Bull. Soc. Chim. Fr.<\/em> 3, 1, 833 1934<\/strong>
    \nFirst paper on the oxidative cleavage of 1,2-diols, now also known as the Malaprade oxidation.<\/li>\n
  2. Chemoselective hydrolysis of terminal isopropylidene acetals and subsequent glycol cleavage by periodic acid in one pot<\/strong>
    \nWenlian Wu and Yulin Wu
    \nThe Journal of Organic Chemistry<\/em> 1993,<\/strong> 58<\/em> (13), 3586-3588
    \nDOI<\/strong>:     10.1021\/jo00065a025<\/a>
    \nThis can be considered a tandem or domino <\/em>reaction \u2013 periodic acid unmasking a diol from an acetal and then oxidatively cleaving it in one pot.<\/li>\n
  3. Eine oxydative Spaltung von Glykolen (II. Mitteil. \u00fcber Oxydationen mit Blei(IV)\u2010salzen)<\/strong>
    \nRudolf Criegee
    \n Ber.<\/em> 1931<\/strong>, 64<\/em> (2), 260-266
    \nDOI<\/strong>:     10.1002\/cber.19310640212<\/a>
    \nThe first paper by on the oxidation of 1,2-diols with Pb(IV) salts, by Rudolf Criegee.<\/li>\n
  4. Direct Titration of cis-Glycols with Lead Tetraacetate<\/strong>
    \nE. Reeves
    \nAnalytical Chemistry<\/em> 1949,<\/strong> 21<\/em> (6), 751-751
    \nDOI<\/strong>:     10.1021\/ac60030a035<\/a>
    \nThis reaction can also be used for the analytical quantification of 1,2-diols, as this paper describes.<\/li>\n
  5. Lead Tetraacetate Oxidations in the Sugar Group. XI. The Oxidation of Sucrose and Preparation of Glycerol and Glycol
    \n<\/strong>Robert C. Hockett and Morris Zief
    \nJournal of the American Chemical Society<\/em> 1950,<\/strong> 72<\/em> (5), 2130-2132
    \nDOI<\/strong>:     10.1021\/ja01161a073<\/a>
    \nPb(OAc)4<\/sub> is commonly used as an oxidant in carbohydrate chemistry, as this paper describes. It is used to cleave 1,2-glycols and differentiate between different kinds of glycol groups.<\/li>\n
  6. (1’R)-(\u2212)-2,4-O-ETHYLIDENE-D-ERYTHROSE AND ETHYL (E)-(\u2212)-4,6-O-ETHYLIDENE-(4S,5R,1’R)-4,5,6-TRIHYDROXY-2-HEXENOATE
    \n<\/strong> Fengler-Veith, O. Schwardt, U. Kautz, B. Kr\u00e4mer, and V. J\u00e4ger
    \n<\/strong>Org. Synth.<\/em> 2002<\/strong>, 78<\/em>, 123
    \nDOI: <\/strong>    10.15227\/orgsyn.078.0123<\/a>
    \nA procedure in Organic Syntheses<\/em> using NaIO4<\/sub> oxidation in carbohydrate chemistry.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"

    Sodium Periodate, NaIO4 As A Reagent In Organic Chemistry In a blatant plug for the\u00a0Reagent Guide \u00a0each Friday \u00a0I profile a different reagent that is <\/p>\n","protected":false},"author":1,"featured_media":16649,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1418],"tags":[168,444,466,450,251,412,264,405],"post_folder":[],"class_list":["post-2517","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkene-reactions","tag-aldehydes","tag-cleavage","tag-diols","tag-naio4","tag-oxidation","tag-reagent-friday","tag-reagent-guide-2","tag-reagents-app"],"acf":[],"yoast_head":"\nReagent Friday: NaIO4 (Sodium Periodate) – Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Sodium periodate, NaIO4, is a useful reagent for the oxidative cleavage of 1,2-diols ("vicinal diols") to give aldehydes and ketones. 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