1,1-, 1,2-, and 1,4-eliminations from the corresponding dihalogenated compounds using Bu3SnSiMe3-F-

Article abstract of DOI:10.1016/0040-4020(96)00376-6

The stannyl anion 2, generated from Me₃SiSnBu₃(1)⁶ in the presence of R₄NX, CsF or TASF [(Et₂N)₃SSiMe₃F₂]⁷ in DMF under very mild conditions, was used for 1,1-, 1,2-,or 1,4-elimination of an aryl or vinyl halide with an appropriate leaving group at the α-, β-, or δ-position of halogen. Thus, alkylidene carbene 8 is generated from 1,1-dibalo-alkene 6 or 7 and benzyne 10 is generated from 1,2-dibromobenzene 9 and an o-quinodimethane 12 was produced from α,α'-dibromoxylene 11a.