
TY  - JOUR
A1  - Josan, JS 
A1  - Eastwood, FW 
T1  - Derivatives of orthoacids. IV. Acid-catalysed thermal eliminations and baseinduced eliminations of some 2-Ethoxy-1,3-dioxolans
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1968
VL  - 21
IS  - 8
SP  - 2013
EP  - 2020
KW  - 
UR  - https://doi.org/10.1071/CH9682013 
N2  - 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. 
ER  -

