STEREOCHEMISTRY OF ASYMMETRIC SILICON .17. SYNTHESIS, RESOLUTION, AND STEREOCHEMISTRY OF 1,2,2,2-TETRAPHENYL-1-METHYLDISILANE SYSTEM

An entirely new route to optically active functionally substituted organosilicon compounds has been developed, by which the 1,2,2,2-tetraphenyl-1-methyldisilane system has been synthesized and resolved. Whereas previously studied systems PhMeRSi*X (R = α-naphthyl, neopentyl, benzhydryl, or ethyl) have nonreacting groups bonded to asymmetric silicon via carbon atoms exclusively, the new system has a nonreacting group bonded to asymmetric silicon via a metalloid-metalloid linkage. Thus far, replacement of an organic R group in PhMe-RSi*X by Ph3Si has not resulted in a reversal of functional group stereochemistry, according to chemical evidence. This extends the validity of earlier stereochemical generalizations for R3Si*X, and reinforces their nondependence on the nature of the nonreacting groups. © 1969, American Chemical Society. All rights reserved.