22086-59-5Relevant academic research and scientific papers
Organoboranes. 29. A convenient synthesis of alkyldibromoboranes and dialkylbromoboranes via hydroboration-redistribution
Brown, Herbert C.,Basavaiah,Bhat
, p. 1309 - 1311 (1983)
Trialkylboranes, obtained via hydroboration of terminal and cyclic alkenes with BH3-SMe2, undergo redistribution with boron tribromide at room temperature under the influence of a catalytic amount (7 mol %) of BH3·SMe2 in n-pentane to afford the corresponding alkyldibromoboranes or dialkylbromoboranes, depending upon the stoichiometry, thus providing a convenient method for preparing these valuable derivatives. The reaction of trialkylboranes derived from internal alkenes such as tri-3-hexylborane is much slower. However, these derivatives could be transformed into the corresponding alkyldibromoboranes at 70°C under neat conditions without significant isomerization. The complete conversion of tri-3-hexylborane into di-3-hexylbromoborane could not be achieved.
α,α-Disubstituted Boron Enolates in the Asymmetric Synthesis of Quaternary Carbon Centers
Burke, E. Diane,Gleason, James L.
, p. 405 - 407 (2007/10/03)
(Equation presented) Reduction of α,α-disubstituted thioglycolate amides with lithium di-tert-butylbiphenylide affords α,α-disubstituted enolates with high Z/E selectivity. Transmetalation of the enolates with dicyclohexylboron bromide facilitates highly
On the relative migratory aptitudes of carbon and heteroatoms in borate complexes. A surprising α-thia effect
Stoddard, Jonathan M.,Shea, Kenneth J.
, p. 830 - 831 (2007/10/03)
Dimethylsulfoxonium methylide reacts with dicyclohexyl(α- thiophenylmethyl)methylborane via 1,2-alkyl migration and alkyldithiaborolane via 1,2-sulfur migration.
Hydroboration with haloborane/trialkylsilane mixtures
Soundararajan, Raman,Matteson, Donald S.
, p. 4157 - 4166 (2008/10/09)
Trialkylsilanes or dialkylsilanes react rapidly with boron trichloride in the absence of ethereal solvents or other nucleophiles to form unsolvated dichloroborane. If no substrate is present, dichloroborane disproportionates to trichloroborane and two geo
