APPLICATIONS OF BAYLIS-HILLMAN COUPLING PRODUCTS - A REMARKABLE REVERSAL OF STEREOCHEMISTRY FROM ESTERS TO NITRILES - A SIMPLE SYNTHESIS OF (2E)-2-METHYLALK-2-EN-1-OLS AND (2Z)-2-METHYLALK-2-ENENITRILES

Reaction of methyl 3-acetoxy-2-methylenealkanoates with the reducing agent, lithium aluminium hydride (LAH): ethanol (1:1), provides (2E)-2-methylalk-2-en-1-ols, whereas, reaction of 3-acetoxy-2-methylenealkanenitriles with the same reagent provides (2Z)-2-methylalk-2-enenitriles in high yields.