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Hydrolysis of Diaryliodonium Salts

Caserio, Marjorie C. and Glusker, Donald L. and Roberts, John D. (1959) Hydrolysis of Diaryliodonium Salts. Journal of the American Chemical Society, 81 (2). pp. 336-342. ISSN 0002-7863. doi:10.1021/ja01511a019.

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The products of hydrolysis of some unsymmetrically substituted diphenyliodonium salts to phenols and aryl iodides have been identified and their distributions determined. The direction of cleavage has been found to be insensitive to the nature of the substituents, the solvent, catalysts, and the nature of the associated anion, fluoride, fluoroborate, p-toluenesulfonate or trifluoroacetate. A rate study has shown that hydrolysis is a complex reaction which is retarded by acid and catalyzed by cuprous copper and also by oxygen when dioxane-water is used as the solvent. Possible mechanisms are discussed.

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Additional Information:© 1959 American Chemical Society. Received May 28, 1958. We are indebted to the John Simon Guggenheim Foundation for support of part of this research. D. L. G. is indebted to the National Science Foundation for a post-doctoral fellowship.
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John Simon Guggenheim FoundationUNSPECIFIED
NSF Postdoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2352
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Official Citation:Hydrolysis of Diaryliodonium Salts Marjorie C. Caserio, Donald L. Glusker, and John D. Roberts Journal of the American Chemical Society 1959 81 (2), 336-342 DOI: 10.1021/ja01511a019
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61339
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 22:39
Last Modified:10 Nov 2021 22:47

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