72420-71-4Relevant academic research and scientific papers
Reactions of Dialkylbromoboranes with Alkali Metal Hydrides in the Presence of Alkenes. Synthesis of 'Mixed' Trialkylboranes (RA2RBB) in Solution
Maddocks, Peter J.,Pelter, Andrew,Rowe, Keith,Smith, Keith,Subrahmanyam, Chitti
, p. 653 - 656 (1981)
Dialkylbromoboranes react steadily with hydroxide-free sodium hydride in diglyme, in the presence of alkenes, to give nearly quantitative yields of partly mixed trialkylboranes.The reaction proceeds too slowly to allow prior clean preparation of dialkylboranes, so reaction in the presence of alkenes possessing hydride-sensitive functional groups is not possible, although terminal alkynes can be hydroborated in situ by a modified experimental procedure.Potassium hydride reacts much more rapidly with dialkylbromoboranes, the reactions being complete within minutes at 20 deg C, but the yields are lower.Addition of dibenzo-18-crown-6 leads to an increase in yield but the results are still inferior to those obtained using sodium hydride.Reaction of dialkylbromoboranes with lithium hydride is very sluggish.
Improved synthesis of tertiary alcohols from reactions of organoboranes with 2-lithio-1,3-benzodithioles
Ncube, Smollie,Pelter, Andrew,Smith, Keith
, p. 1895 - 1896 (2007/10/05)
Treatment of trialkylboranes with 2-lithio-1,3-benzodithioles and then mercuric chloride (or methyl fluorosulhonate) followed by oxidation gives tertiary alcohols in high yields. The method is applicable to reactions of hindered organoboranes that fail using 1-lithio-1,1-bis(phenylthio)alkanes.
