Exchange Reactions of Organotin and Organosilicon Compounds with MildFluorinating Agents

摘要

A diverse group of compounds bearing labile fluorine atoms have been found toundergo similar exchange reactions with various organosilanes and stannanes. For example, methylphosphonic difluoride, boron trifluoride etherate, and perfluoroisobutene all react with both organosilicon and organotin alkoxides to give products resulting from the exchange of fluoride for an alkoxide group. In contrast to reactions involving the use of protic nucleophiles that may yield these products, hydrogen fluoride is not formed as a byproduct in these systems. Organotin compounds have been found to be more reactive than their silicon based analogs. Mechanisms are proposed to account for the products and the reactivity differences observed in these systems. These reactions have proven useful for the routine synthesis of various compounds. Perfluoroisobutene Organotin esters Tributyltin methoxide Addition-elimination Or anosilicon esters Tributyltin cyanide.