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Issue 5, 2007
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Oxidative cleavage of vicinal diols: IBX can do what Dess–Martin periodinane (DMP) can

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Abstract

The fact that IBX exhibits reactivity akin to DMP is demonstrated from the results observed with strained and sterically hindered syn 1,2-diols, which undergo oxidative cleavage via a 12-I-5 spirobicyclic periodinane. The use of TFA, a protonating solvent, promotes the formation of the 12-I-5 intermediate for 1,2-diols of all types (sec,sec, sec,tert and tert,tert), leading to efficient oxidative fragmentation.

Graphical abstract: Oxidative cleavage of vicinal diols: IBX can do what Dess–Martin periodinane (DMP) can

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Publication details

The article was received on 12 Dec 2006, accepted on 16 Jan 2007 and first published on 30 Jan 2007


Article type: Communication
DOI: 10.1039/B618135J
Citation: Org. Biomol. Chem., 2007,5, 767-771
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    Oxidative cleavage of vicinal diols: IBX can do what Dess–Martin periodinane (DMP) can

    J. N. Moorthy, N. Singhal and K. Senapati, Org. Biomol. Chem., 2007, 5, 767
    DOI: 10.1039/B618135J

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