Synthesis of difunctional 1,4-dimethyl-1,4-disilacyclohexanes

Article abstract of DOI:10.1007/BF02494818

Transformations of HVinSiCl₂, HVinSi(Me)Cl, HVinSi(Me)Ph, and HVinSi(Me)NEt₂ in the presence of Pt catalyst were studied. In dilute solutions, the reaction gave a mixture of structural and stereoisomers of five- and six-membered disilacyclanes, resulting from intramolecular cyclization of the initially formed linear dimer. In the case of methyl(phenyl)disilacyclane, the structural isomers were separated and tran.s-1,4-dimethyl-1,4-diphenyl-1,4-disilacyclohexane was isolated. The reaction of this product with HCI in the presence of AlCl₃ followed by hydrolysis resulted in the synthesis of trans-1,4-dichloro- and trans-1,4-dihydroxy-1,4-dimethyl-1,4-disilacyclohexanes. The structures of the structural and stereoisomers synthesized were confirmed by ¹H, ¹³C, and ²⁹Si NMR and IR spectroscopies and mass spectrometry.