Preparative Organic Chemistry
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ChemInform Abstract: Iodination of (E)-2,2,5,5-Tetramethyl-3,4-diphenylhex-3-ene: Catalytic Effects of Silver Triflate and Water in the I2/Ag2SO4 Iodination.
First published: 24 June 2010
Abstract
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ChemInform Abstract
Whilst conventional iodination of the title olefin fails, AgOTf-catalyzed reaction with I2/Ag2SO4 provides a mixture of mono- and diiodinated products (II) and (III), respectively. Success is shown to be dependent upon the presence of a trace of water in the solvent. The method is usefully extended to the iodination of reluctant arenes [cf. (IV), (VII)].
