Collect. Czech. Chem. Commun. 1990, 55, 704-709

Preferential cis-olefin formation: A striking resemblance between alkali-alkoxide and alumina promoted eliminations in low polar solvents

Jiří Závada and Magdalena Pánková

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Olefin-isomer distribution has been investigated in the Woelm alumina promoted elimination from a series of 2-decyl and 5-decyl derivatives (X = F, Cl, Br, I, OTs) in ether. From the observed effect of leaving group it has been inferred that the heterogeneous reaction is a concerted process. A comparison has been made with corresponding results from homogeneous, alkali-alkoxide promoted eliminations in low polar solvents. A striking similarity in steric course between the two reactions has been noted and explained in terms of acid-base co-catalysis.