MIGRATION OF ARYL GROUPS FROM SILICON TO CARBON IN ALPHA,BETA-EPOXYSILANES - A NEW MODEL FOR HYPERVALENT SILICON STUDY

The reaction of (2R,3R)-3-(triphenylsilyl)glycidol (1) with n-Bu4NF . 3H(2)O in THF, followed by treatment of the product with p-nitrobenzoy l chloride yields (2S)-glycidol p-nitrobenzoate (4) and trans-cinnamyl p-nitrobenzoate (6) in a ratio of 1:1.5. The reaction of (R)Si-(2R,3R )- or )-3-[(methyl)(phenyl)(1-naphthyl)silyl]-glycidols, 7 or 8 respec tively, with n-Bu4NF . 3H(2)O affords mixtures of the respective glyci dol, trans-cinnamyl alcohol and 3-(1-naphthyl)allyl alcohol. No signif icant difference in the product distribution in reaction of these two diasteromers was observed. (C) 1998 Elsevier Science S.A. All rights r eserved.