REACTION OF PROPARGYL BROMIDE AND TRIMETHYLSILYLPROPARGYL IODIDE WITH METALLIC TIN, ALUMINUM, AND ALDEHYDES OR KETONES. SELECTIVE SYNTHESIS OF β-ACETYLENE, β-TRIMETHYLSILYLACETYLENE, AND α-TRIMETHYLSILYLALLENE ALCOHOLS

β-Acetylenic and α-allenic alcohols were synthesized selectively by the reaction of aldehydes and ketones with organotin compounds prepared by treatment of propargyl bromide or trimethylsilylpropargyl iodide with metallic tin and aluminum in a suitable solvent.