Reactions of trimethylsilyl-derived iodohydrins with electron-rich π-systems†
Abstract
Reactions of CH–OTMS), and 1,1-diarylethylenes were the
O reacted smoothly in the presence of TMSI to yield the condensation product RCH2–CH
C(R)–CH
O. Both RCH(–CH
CAr2)2 and the
O–TMSI–CH2
CAr2
reaction system, depending on the [RCHO] ∶ [TMSI] ∶ [CH2
CAr2] concentration ratio. The mechanisms of formation for the various main products and by-products are discussed. TMSI substitutes, formed by reacting Me3SiCl with each of several Lewis acids, were also used.