The cyclic silyl ethers, 2,2-dimethyl-1-oxa-2-slia-3-cyclopentenes, were pr
oduced by the treatment of (2)-gamma -trimethylsilyl allylic alcohols with
a catalytic or stoichiometric amount of lithium tort-butoxide. On the other
hand, successive treatment of the alcohols with copper(l) tert-butoxide an
d allylic halides followed by the tetrabutylammmonium fluoride assisted hyd
rolysis produced the allylation products, 2,5-alkadien-1-ols, with complete
retention of configuration of the double bond.