References
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Crocker wants Timmy to research IBX reactions. Timmy finds a paper which he references as: Then he notices that this article was used as a reference in several other papers as well…. “m-Iodosylbenzoic acid as a convenient recyclable reagent for highly efficient RuCl3-catalyzed oxidation of alcohols to carbonyl compounds” Yusubov MS, Gilmkhanova MP, Zhdankin VV, Synlett, 2007, 4, 563-566 “N-(2-iodylphenyl)acylamides - New pentavalent iodine oxidizing reagents” Ladziata U, Zhdankin VV, Synlett, 2007, 4, 527-537 “Preparation and reactivity of polymer-supported 2-iodylphenol ethers, an efficient recyclable oxidizing system” Karimov RR, Kazhkenov ZGM, Modjewski MJ, Journal of Organic Chemistry, 2007, 21, 8149-8151 The main article details the mechanism of IBX reactions (see the IBX lesson). Which is a reagent used to convert primary and secondary alcohols to aldehydes and keytones in high yields. The first step of the reaction starts when the oxygen double bonded to the iodine is protonated. Then the alcohol of target molecule (in our reaction 139) attacks the iodine. The conjugate acid then removes the hydrogen from the alcohol group restoring the neutrality of the molecule. A base then deprotonates the carbon attached to the oxygen in the elimination step which releases the IBX molecule. If the alcohol was primary an aldehyde is formed (as in this reaction). If the alcohol was secondary, a keytone forms. The other articles all use IBX to convert alcohols to aldehydes and keytones. Crocker was not impressed and gave Timmy an F anyways. |