Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 5, Issue 5, Pages 767-771Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b618135j
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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.
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