INFLUENCE OF A SILYL GROUP ON AN ALLYLIC POSITION. A THEORETICAL APPROACH

Article abstract of DOI:10.1016/0040-4020(80)80114-1

Allylsilanes show in certain cases a behaviour towards electrophiles which is opposite to that of its carbon homologues.Theoretical calculations using Dewar's MINDO/3 method performed on 3-methyl 3-butenyl trimethyl-silane and 2-methyl 2-butene show that geometrical optimization leads to a silicon-allylic carbon bond nearly parallel to the double bond ? cloud, and both net atomic charges and HOMO coefficients indicate an inversion between these two substrates.