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Molecules 2015, 20(12), 21415-21420; doi:10.3390/molecules201219773

Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid

Department of Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan
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Author to whom correspondence should be addressed.
Academic Editor: Thomas G. Back
Received: 1 November 2015 / Revised: 18 November 2015 / Accepted: 25 November 2015 / Published: 2 December 2015
(This article belongs to the Special Issue Selenium Catalysts and Antioxidants)
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Abstract

A primary-alkyl-substituted selenenyl iodide was successfully synthesized through oxidative iodination of a selenol with N-iodosuccinimide by taking advantage of a cavity-shaped steric protection group. The selenenyl iodide exhibited high thermal stability and remained unchanged upon heating at 100 °C for 3 h in [D8]toluene. The selenenyl iodide was reduced to the corresponding selenol by treatment with dithiothreitol. Hydrolysis of the selenenyl iodide under alkaline conditions afforded the corresponding selenenic acid almost quantitatively, corroborating the chemical validity of the recent proposal that hydrolysis of a selenenyl iodide to a selenenic acid is potentially involved in the catalytic mechanism of an iodothyronine deiodinase. View Full-Text
Keywords: selenenyl iodide; selenenic acid; hydrolysis; kinetic stabilization; iodothyronine deiodinase selenenyl iodide; selenenic acid; hydrolysis; kinetic stabilization; iodothyronine deiodinase
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MDPI and ACS Style

Sase, S.; Kakimoto, R.; Kimura, R.; Goto, K. Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid. Molecules 2015, 20, 21415-21420.

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