Abstract
The reaction of the bulky Eind-based dialumane, (Eind)HAl(μ-H)2AlH(Eind) (1) (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl), with pyridines is described. When 1 was treated with pyridine (Py) in toluene, the Py adduct of aryldihydroalumane, Py→AlH2(Eind) (2), was initially formed. Then, the hydroalumination of Py took place to yield the Py-bound aryl(1,4-dihydropyrid-1-yl)hydroalumane, Py→AlH(1,4-dihydropyrid-1-yl)(Eind) (3). A similar reaction with a stronger Lewis base, 4-pyrrolidinopyridine (PPy), produced the stable PPy adduct, PPy→AlH2(Eind) (4). The resulting organoaluminum compounds have been fully characterized by NMR spectroscopy as well as X-ray crystallography. The reaction mechanism from 1 to 3 via 2 has been examined by deuterium labeling experiments using (Eind)DAl(μ-D)2AlD(Eind) (1-d4).
Highlights
Aluminum hydrides have been widely used as a powerful reducing agent both in inorganic and organic synthesis, whose excellent reactivities are primarily based on polarized Al–H bonds due to the rather electropositive aluminum atom [1,2,3,4,5,6,7,8]
The aggregation behavior and structural characteristics of the hydrogen-substituted aluminum compounds both in solution and in the solid state have been investigated for many years to understand their unique chemical bonding arising from the electron deficiency of the group 13 elements [1,2,3,4,5,6,7,8]
Tanner and Yang reported the detailed studies of the reaction between LiAlH4 and Py; five isomers of lithium tetrakis(dihydropyridyl)aluminate having 1,2- or
Summary
Aluminum hydrides have been widely used as a powerful reducing agent both in inorganic and organic synthesis, whose excellent reactivities are primarily based on polarized Al–H bonds due to the rather electropositive aluminum atom [1,2,3,4,5,6,7,8]. Tanner and Yang reported the detailed studies of the reaction between LiAlH4 and Py; five isomers of lithium tetrakis(dihydropyridyl)aluminate having 1,2- or. Hensen et al reported the crystal structures of lithium tetrakis(1,4-dihydropyrid-1-yl)aluminate and related aluminate compounds determined by an X-ray diffraction analysis [13]. They examined the hydroalumination of Py using a neutral trihydroalumane-trimethylamine complex, Me3 N→AlH3 , yielding the Py-coordinated tris(1,4-dihydropyrid-1-yl)alumane [13].
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