Cleavage of an Si–Me bond by intramolecular alkoxide-ion attack. Crystal structure of 6,6-bis(trimethylsilyl)norbornan-endo-2-ol

Abstract

The crystal structure of the title alcohol, 2, has been determined in order to throw light on the ease of intramolecular displacement of a Me group to give 3 when 2 is treated with Bu^tOK–Bu^tOH. In 2(and thus presumably in the alkoxide ion derived from it) the O-atom and the endo-SiMe₃ group are held in a very favourable disposition for this displacement, and because of this, and the high rigidity of the substrate molecule, there is little loss of entropy on going to the cyclic transition state.