Synthesis, stereochemistry, and crystal and molecular structure of endo-3-methyl-exo-3-hydroxy-3-silabicyclo[3.2.1]octane

Abstract

The structure of the title compound was determined by an X-ray diffraction study. The crystals are monoclinic, a= 21.733(2), b= 10.328(1), c= 8.587(2)Å, β= 105.39(1)°, space group C2/c, Z= 8. The structure was solved by direct methods from diffractometer data and refined to an R value of 0.053. The silacyclohexane ring in this bicyclic system adopts a chair conformation which is substantially flattened at the silicon end. The endo-disposition of the 3-methyl substituent was confirmed by this study. The bond angles and distances are in close agreement with those in endo-3-methyl-3-silabicyclo[3.2.1]octane as determined by molecular mechanics calculations and gas-phase electron diffraction.