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. IBX (below) looks very similar to the Dess-Martin periodinane. MeO IBX (2-lodoxybenzoic acid) Although Dess-Martin has mostly replaced IBX due to rumors of IBX's explosive nature, use their analogous structures to propose a reasonable mechanism for the IBX reaction below. OH OH IBX H₂O MeO H

. IBX (below) looks very similar to the Dess-Martin periodinane. MeO IBX (2-lodoxybenzoic acid) Although Dess-Martin has mostly replaced IBX due to rumors of IBX's explosive nature, use their analogous structures to propose a reasonable mechanism for the IBX reaction below. OH OH IBX H₂O MeO H

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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### IBX Reactivity and Mechanism #### Introduction IBX (2-Iodoxybenzoic acid) is chemically similar to the Dess-Martin periodinane. Despite its structural likeness, Dess-Martin is often preferred, primarily due to safety concerns regarding IBX's potentially explosive nature. #### Structure of IBX - The structural formula for IBX displays a benziodazolone core with additional oxygen functionalities that are key to its reactivity. #### Chemical Reaction A proposed reaction involves IBX as an oxidizing agent: 1. **Starting Material**: A methoxy-substituted benzyl alcohol. 2. **Reagent**: IBX in the presence of water (H₂O). 3. **Product**: A corresponding methoxybenzaldehyde is formed, indicating the oxidation of the alcohol to an aldehyde. #### Mechanism Proposal Using the analogous structure of Dess-Martin, one can propose a reasonable mechanism wherein the alcohol group is oxidized to an aldehyde by the action of IBX, with possible intermediates and transition states involving the reorganization of iodine-oxygen bonds. The process preserves the aromatic system and introduces a carbonyl functionality. This guide thus outlines the conceptual framework for understanding IBX's function in organic synthesis, with its application marred by stability concerns.
Transcribed Image Text:### IBX Reactivity and Mechanism #### Introduction IBX (2-Iodoxybenzoic acid) is chemically similar to the Dess-Martin periodinane. Despite its structural likeness, Dess-Martin is often preferred, primarily due to safety concerns regarding IBX's potentially explosive nature. #### Structure of IBX - The structural formula for IBX displays a benziodazolone core with additional oxygen functionalities that are key to its reactivity. #### Chemical Reaction A proposed reaction involves IBX as an oxidizing agent: 1. **Starting Material**: A methoxy-substituted benzyl alcohol. 2. **Reagent**: IBX in the presence of water (H₂O). 3. **Product**: A corresponding methoxybenzaldehyde is formed, indicating the oxidation of the alcohol to an aldehyde. #### Mechanism Proposal Using the analogous structure of Dess-Martin, one can propose a reasonable mechanism wherein the alcohol group is oxidized to an aldehyde by the action of IBX, with possible intermediates and transition states involving the reorganization of iodine-oxygen bonds. The process preserves the aromatic system and introduces a carbonyl functionality. This guide thus outlines the conceptual framework for understanding IBX's function in organic synthesis, with its application marred by stability concerns.
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