Journal
COORDINATION CHEMISTRY REVIEWS
Volume 250, Issue 21-22, Pages 2771-2781Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.ccr.2006.04.017
Keywords
I(III)O-...; complexation; crown ethers; hypervalent interactions; iodine; bromine; iodosylbenzene; oxidations
Categories
Ask authors/readers for more resources
In this account, we show that intermolecular hypervalent I(III)...O interactions play an essential role in the complexation of organo-lambda(3)-iodanes with crown ethers. In addition to the well-known driving force for the complexation of crown ethers, ion-dipole interaction, and hydrogen bonding interaction, our result provides a new class of interaction in supramolecular chemistry of crown ethers. Both solid state structure analysis and solution chemistry indicate that diaryl-, 1-alkynyl(phenyl)-, and 1-alkenyl(phenyl)-lambda(3)-iodanes as well as 1-alkynyl(aryl)-lambda(3)-bromanes form stable complexes with 18-crown-6 through hypervalent I(III)...O or Br(III)...O interactions. In these complexes, hypervalent iodine(III) or bromine(III) atom contacts with the three adjacent oxygen atoms of 18-crown-6. The complexation not only increases the stability of these hypervalent compounds but also increases the solubility toward polar solvents. The highly labile, activated iodosylbenzene monomers were isolated as stable crystalline complexes by the coordination of 18-crown-6. These iodosylbenzene monomer complexes serve as versatile oxidizing agents, especially in water as a solvent. (c) 2006 Elsevier B.V. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available