34611-76-2Relevant academic research and scientific papers
Organoboranes. 47. An extremely facile elimination of alkenes from dialkylhaloboranes. A comparative rate study with related trialkylboranes
Brown, Herbert C.,Ramachandran,Chandrasekharan
, p. 2138 - 2141 (1986)
Dialkylhaloboranes reduce benzaldehyde at a rate much faster than does trialkylboranes. Whereas Ipc2BCl reduces 2 equiv of benzaldehyde at room temperature almost instantaneously, the related trialkylborane Ipc2B-n-Hex requires approximately 6 days. Sia2BCl, 2-MeCpn2BCl, Car2BCl and Ipc2BBr also reduce benzaldehyde rapidly, but 2-MeChx2BCl reacts relatively slowly. A cyclic mechanism with a boat-like transition state is proposed, which can account for the major differences in the rates of reduction among the various dialkylhaloboranes.
