
%0 Journal Article
%A Josan, JS 
%A Eastwood, FW 
%T Derivatives of orthoacids. IV. Acid-catalysed thermal eliminations and baseinduced eliminations of some 2-Ethoxy-1,3-dioxolans
%J Australian Journal of Chemistry
%D 1968/08/01
%V 21
%N 8
%P 2013-2020
%K 
%R https://doi.org/10.1071/CH9682013
%U https://www.publish.csiro.au/paper/CH9682013 
%X 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. 
