Metalation reactions XIII. The reactions of electrophiles with the dilithiated species 1-(α-lithiomethyl)-2-benzene

Article abstract of DOI:10.1016/0022-328X(89)87310-3

Direct dimetalation of 1-methyl-2-(methylthio)benzene (1) gives the dilithiated species (2) in good yield, which can be used to introduce substituents into the thiomethyl and methyl groups.Species 2 can react also with a variety of dichlorosilanes and dichlorostannanes, and with sulphur chloride, to yield derivatives of 1,3-benzothiasilin, 1,3-benzothiastannin and 1,3-benzodithiin respectively.Reaction of 2 with tetrachlorosilane yields a spirocyclic silicon compound, while reaction with benzoyl chloride yields a derivative of 1-benzothiopyran.