Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
The Journal of Organic Chemistry2011Vol. 76(23), pp. 9593–9601
Citations Over TimeTop 10% of 2011 papers
Jarugu Narasimha Moorthy, Kalyan Senapati, Keshaba Nanda Parida, Samik Jhulki, Sooraj Kunnikuruvan, Nisanth N. Nair
Abstract
The methyl groups in TetMe-IBX lower the activation energy corresponding to the rate-determining hypervalent twisting (theoretical calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility in common organic solvents. Consequently, oxidations of alcohols and sulfides occur at room temperature in common organic solvents. In situ generation of the reactive TetMe-IBX from its precursor iodo-acid, i.e., 3,4,5,6-tetramethyl-2-iodobenzoic acid, in the presence of oxone as a co-oxidant facilitates the oxidation of diverse alcohols at room temperature.
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