FLUORINATION WITH XENON DIFLUORIDE, PART XXXV. REACTION WITH GRIGNARD REAGENTS

Article abstract of DOI:10.1016/S0022-1139(00)83938-X

Several Grignard reagents in diethyl ether solution readily react with xenon difluoride at room temperature, the complexity of the reaction course depending on the structure of the reagent.In all cases studied three main types of products, i.e. 1-ethoxy-1-substituted ethane (2), reduced product (3) and dimeric product (4) are formed.In the case of dodecyl magnesium bromide (1a), 2-ethoxydodecane (2a), decane (3a) and eicosane (4a) formed represent 98percent of products formed, with 2percent of the reaction mixture containing at least up to seven unidentified products, while with benzyl magnesium bromide (1b), the three main products 2b, 3b, and 4b represent 80percent of the reaction mixture, the remaining 20percent containing up to nine products with benzyl bromide being the main side product.The complexity of the reaction increases even more in the case of phenyl magnesium bromide, where 2c, 3c and 4c represent only 70percent of products formed, the remaining 30percent consisting of up to 21 products with the following being identified: bromobenzene, bromobiphenyl, 1,1-bromo-1-phenylethane, α-bromo and α,α-dibromoacetophenone, and 1,1-diphenyl-2-bromoethene.