STEREOCHEMISTRY OF ASYMMETRIC SILICON .12. REACTIONS OF SILICON-OXYGEN AND SILICON-NITROGEN COMPOUNDS WITH BORON HALIDES

The stereochemistry of the reactions of a variety of optically active alkoxysilanes and aminosilanes with boron halides has been studied. For these reactions, which yield the halosilane, the simplest and most obvious mechanistic possibility would be a four-center mechanism and this has been previously proposed by other authors. We have found that most of the reactions proceed with inversion of configuration. (The major exception is BCl3 plus R3Si*ORʹ.) Thus, clearly, the general mechanistic situation is not the one previously assumed and the present paper discusses new mechanistic possibilities for these interesting reactions of asymmetric silicon with strong Lewis acids. © 1969, American Chemical Society. All rights reserved.