Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can |
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Authors: | Moorthy Jarugu Narasimha Singhal Nidhi Senapati Kalyan |
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Affiliation: | Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. moorthy@iitk.ac.in |
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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. |
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