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Oxidative Cleavage of Olefins by In Situ-Generated Catalytic 3,4,5,6-Tetramethyl-2-iodoxybenzoic Acid/Oxone

Jarugu Narasimha Moorthy* and Keshaba Nanda Parida

*Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India, Email: moorthyiitk.ac.in

J. N. Moorthy, K. N. Parida, J. Org. Chem., 2014, 79, 11431-11439.

DOI: 10.1021/jo502002w (free Supporting Information)


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Abstract

Oxidative cleavage of various olefins to the corresponding ketones/carboxylic acids occurs with catalytic amounts of 3,4,5,6-tetramethyl-2-iodobenzoic acid (TetMe-IA) and oxone as terminal oxidant in acetonitrile-water mixture at rt. The reaction mechanism involves dihydroxylation of the olefin with oxone, oxidative cleavage by TetMe-IBX, and oxidation of the aldehyde functionality to the corresponding acid with oxone.

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Key Words

oxidative cleavage, hypervalent iodine compounds, oxone


ID: J42-Y2014