Selective Hydroboration of Double Bonds in the Presence of Triple Bonds by 9-Borabicyclo[3.3.1]nonane. New Route to Acetylenic Organoboranes and Alcohols

Hydroboration of acetylenes with 9-borabicyclo[3.3.1]nonane is slow compared to hydroboration of structurally similar olefins, in direct contrast to the relative ease of hydroboration with other dialkylboranes. This unexpected reactivity allows clean selective hydroboration of double bonds in the presence of triple bonds and formation of acetylinic organoboranes directly from readily available allylic acetylenes. © 1979, American Chemical Society. All rights reserved.