Yields and Stereoselectivities of Chlorinolysis of Trialkylboranes. Comparison of a Variety of Selected Methods

Article abstract of DOI:10.1021/jo00259a010

Yields and stereoselectivities for chlorinolysis of a series of representative trialkylboranes R3B (R = pentyl, hexyl, cyclohexyl, sec-butyl, exo-2-norbornyl) with a variety of chlorinolysis methods (CuCl2/H2O; FeCl3; dichloramine T; NCl3; t-BuOCl) are compared.Of the easily handled reagents, dichloramine T generally gives good yields and is most stereoselective (>99percent exo:<1percent endo-2-norbornyl chloride).Yields and stereoselectivities of chlorinolysis with tert-butyl hypochlorite were higher in pentane than in tetrahydrofuran solvent.