A rearranged acetylene from an E1 solvolysis of a substituted α-trimethylsilylvinyl system

Article abstract of DOI:10.1016/0040-4039(91)80177-8

The reaction of Mes₂C=C(OH)SiMe₂R (R=Me, SiMe₃) with SOCl₂ gives the rearranged elimination product MesC≡CMes, presumably via β-mesityl participation in the solvolysis of the derived OSOCl derivative, followed by 'Me₃Si⁺' loss from the rearranged ion MesC(Me₃Si)=C-Mes. Under the same conditions, the carbon analogue Mes₂C=C(OH)Bu-t gives the ketone Mes₂CHCOBu-t and benzofurans via non-solvolytic reactions.