Fluorous solvents (perfluoroalkanes) are very unique in their solubility and miscibility properties.1  At room temperature, they are generally immiscible with aqueous and organic solutions.  They dissolve molecules with perfluoroalkyl-tags but not normal organic compounds.  At elevated temperatures, their solubility of normal organic compounds increase and some organic solvents become miscible with fluorous solvents.  Using perfluoroalkyl-tagged reagents, with incorporation of these fluorous solvents' unique properties, could have both of the advantages of monophasic reactions and biphasic separation from products.             In this presentation, the synthesis of a variety of new perfluoroalkyl-tagged iodoarenes2 will be reported.  Their conversion to iodine(III) dichlorides will be described, and the fluorous/organic partition coefficients of all new compounds will be detailed.  New types of biphasic hydrocarbon chlorination reactions will be described.  After reaction, the perfluoroalkyl-tagged iodoarene byproducts can selectively be solubilized in fluorous solvents, facilitating recovery and recycling.1. Gladysz, J. A.; Curran, D. P.; Horv�th, I. T. Handbook of Fluorous Chemistry; Wiley-VCH: Weinheim, 2004 .2. Podgor�ek, A.; Jurisch, M.; Stavber, S.; Zupan, M.; Iskra, J.; Gladysz, J. A. J. Org. Chem. 2009 , 74, 3133-3140.

Perfluoroalkyl-tagged aryliodine(III) chlorination reagents

246th National Meeting (2013)

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