About the stereoelectronics of the intramolecular addition of allylsilanesto aldehydes

(Z)-omega -Trimethylsilyl-(omega -2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega -1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z) -omega -trimethylsilyl-(omega -2)-alkenals which, in the presence of triflu oroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylc yclohexanol (2), isopulegol (4), and bis(2 vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interfer ence of a novel electrodynamic effect.