Allylmanganation and Diallylation of Acetylenic Compounds.

Abstract Treatment of homopropargylic alcohol and its derivatives or propargylic alcohols with tetraallylmanganate or triallylmanganate provided monoallylated products in good yields with high regio- and stereoselectivities. The intermediary alkenylmanganese compounds were trapped by various electrophiles. The reaction was clearly oxygen-assisted since 6-dodecyne was completely recovered unchanged. Diallylation products were obtained in the presence of air. Allylmagnesation and diallylation of these acetylenic compounds catalyzed by manganese salts are also disclosed.