Vinyl Ethers Containing an Epoxy Group:XXIII.*Reactions of Alkynylmagnesium Bromides with Glycidol Ethers:Synthesis and Thermal Transformations of 1-[2-( Vinyloxy)ethoxy]- and 1-(Allyloxy)-5-hexyn-2-ols,-5-phenyl-4-pentyn-2-ols,and -3-bromo-2-propano

摘要

Reaction of 2-[2-(vinyloxy)ethoxy]methyl- and 2-(allyloxymethyl)oxiranes with 2-propynyl- and phenylethynylmagnesium bromides (10-55 deg C,0.5-4 h) resulted in new representatives of the series of 1-organyloxy-5-hexyn-2-ols,-5-phenyl-4-pentyn-2-ols,and -3-bromo-2-propanols in 50-99% yields.During distillation the 1 -[2-(vinyloxy)ethoxy]-5-phenyl-4-pentyn-2-ol and -3-bromo-2-propanol transform respectively into 2-methyl-4-(3-phenyl-2-propynyl)-and 2-methyl-4-(bromomethyl)-1,3,6-trioxocanes via intramolecular cyclization involving the hydroxy and vinyloxy groups.