<i>Ortho</i>-Silylated Derivatives of Tetrakis(2-hydroxyphenyl)ethene: A Sterically Isolated Structural Model for Oxo-Surface Binding Domains

The introduction of sterically isolating ortho-trialkylsilyl, -aryldialkylsilyl, and -diarylalkylsilyl substituents onto the structurally preorganized tetrakis(2-hydroxyphenyl)ethene ligand framework has been accomplished by a 4-fold retro-Brook rearrangement. Installation of the most sterically demanding silyl substituents required the development of an iterative procedure, involving successive double silylation/metalation/migration sequences without the isolation of intermediates. This system was designed to function as a soluble structural model for the planar binding domains of heterogeneous “oxo-surfaces” of silica and alumina supports.