Hydroalumination of alkenes by the LiAlH4*3AlBr3 system

Article abstract of DOI:10.1007/BF00699198

The hydroalumination of a series of alkenes and some fused aromatic hydrocarbons by the LiAlH4*3AlBr3 system in low-polar solvents was studied.Alkenes with mono-, di-, tri-, and tetraalkyl substituted, mono- and diaryl substituted double bonds and anthracene react at room temperature to give the corresponding dibromoaluminoalkanes in high yields.Benzylidenefluorene, tetraphenylethylene, naphthalene, and phenanthrene do not undergo hydroalumination under these conditions.Camphene, bicyclo<3.2.1>oct-2-ene, and norbornene afford the corresponding organoaluminum compounds with high stereoselectivity.Oxidation and halo- and acyldemetallation of the resulting alkyl- and arylalanes were carried out.