Abstract
This chapter reviews Donald J. Burton group's research activities in Iowa. He pursued the aluminum halide-catalyzed rearrangement and disproportionation of fluorohaloalkanes and fluorohaloallyl halides as a PhD topic. Frank Herkes, one of the first graduate students who joined his research group at Iowa in 1962, piqued his initial interest in ylide chemistry. They established a new route to β-phenyl-substituted perfluoroolefins. This venture initiated their work in ylide chemistry. In addition to the fluoromethylene ylides, they also pioneered the preparation and identification of stable fluorinated cyclic ylides. Donald J. Burton also worked on carbenes and organometallic chemistry. Conjugated enynes provide an efficient method for the assembly of multifunctional molecules and one would anticipate that fluorine-containing enynes would be useful building blocks to partially fluorinated multifunctional molecules or partially fluorinated natural products. Interest in the generality of palladium-catalyzed coupling reactions of fluorinated vinyl and aryl iodides directed them to investigate the utility of these precursors in enyne and/or alkyne preparations. From the experience in Professor H. C. Brown's laboratory, he carried an interest in metal hydride and borane chemistry with him to the University of Iowa.
Published Version
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