| Abstract
| - The efficient formation of single-isomer, differentially halogenated alkenes and alkanes is described.These structures were generated by treatment of the appropriate alkyne or alkene with tetrabutylammoniumiodide in refluxing dichloroethane. This process is highly selective as evidenced by control experimentsusing ICl. Treatment of the same alkenes and alkynes directly with iodine monochloride resulted incomplex, inseparable mixtures of regio- and stereoisomers. Mechanistic studies indicated that the Bu4NIreaction most likely proceeded through the slow generation of ICl. Complexation of ICl with Bu4NI isalso a key controlling element that leads to perfect regio-, chemo-, and stereoselectivity in these processes.
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