The reaction of α-haloepoxides with zinc powder or reagents containing the trialkylstannate anion yields allylic alcohols by anti elimination of the carbon halogen and adjacent carbon epoxy oxygen bonds. Appreciable Z→ E isomerization occurs in both types of reactions but the experimental results indicate that the conversion of erythro α-bromoepoxides to E allylic alcohols by zinc or trialkylstannates shows sufficient stereospecificity to be synthetically ...
