2-Iodylphenol Ethers:  Preparation, X-ray Crystal Structure, and Reactivity of New Hypervalent Iodine(V) Oxidizing Reagents

Alexey Y. Koposov, Rashad R. Karimov, Ivan M. Geraskin, Victor N. Nemykin,* and Viktor V. Zhdankin*;
Department of Chemistry and Biochemistry, University of MinnesotaDuluth, Duluth, Minnesota 55812
J. Org. Chem., 2006, 71 (22), pp 8452–8458
DOI: 10.1021/jo0614947
Publication Date (Web): September 23, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, vzhdanki@d.umn.edu, ; , vnemykin@d.umn.edu

Abstract

Abstract Image

2-Iodylphenol ethers were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenol ethers and isolated as chemically stable, microcrystalline products. Single-crystal X-ray diffraction analysis of 1-iodyl-2-isopropoxybenzene 8c and 1-iodyl-2-butoxybenzene 8d revealed pseudopolymeric arrangements in the solid state formed by intermolecular interactions between IO2 groups of different molecules. 2-Iodylphenol ethers can selectively oxidize sulfides to sulfoxides and alcohols to the respective aldehydes or ketones.

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History

  • Published In Issue October 27, 2006
  • Received July 18, 2006

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