A series of phenyl
substituted 2-ethoxy-1,3-dioxolans (orthoformates) has been prepared and their
stereochemistry assigned. When heated in the presence of a carboxylic acid they
underwent a stereospecific cis elimination
to form the corresponding olefins, carbon dioxide, and ethanol. Provided that
one 4 or 5 position in these dioxolans was unsubstituted, they reacted with
butyllithium through elimination of the elements of ethyl formate and the
formation of a carbonyl compound. The eliminated portion was always converted
by the butyllithium into nonan-5-ol. A simple preparative method for cis-stilbene is described.
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