Novel synthesis of an ω-alkynylorganometallic reagent via triple bond isomerization with potassium 3-aminopropylamide: ω-(9-borabicyclo[3.3.1]nonan-9-yl)alkl-1-ynes

Abstract

Isomerization of 1-(9-borabicyclo[3.3.1]nonan-9-yl)oct-4-yne, readily prepared by hydroboration of oct-1-en-4-yne with 9-borabicyclo[3.3.1]nonane and 2·5–3·0 equiv. of potassium 3-aminopropylamide, yields quantitatively 1-(9-borabicyclo[3.3.1]nonan-9-yl)oct-7-yne, which undergoes typical organoborane, reactions such as oxidation and alkyltransfer to α-bromoketones.