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- W2085909175 abstract "Abstract In order to evaluate steric and electronic factors in the hydralumination of pπ- and dπ-conjugated olefins, the following compounds have been treated with diisobutylaluminum hydride: 1,1-diphenylethylene; 1,1-diphenylallene; 1,1-diphenyl-1,3-butadiene; acenaphthylene; triethylvinylsilane; and triphenylvinylsilane. The sites of the resulting carbon—aluminum bonds in the adducts have been deduced by a combination of NMR spectroscopy, hydrolysis with D2O, oxidation and carbonation. Hydralumination of 1,1-diphenylethylene gave only the 1,1-diphenyl-2-aluminoethane adduct; 1,1-diphenylallene gave a mixture of the 3-alumino-1,1-diphenyl- and 3-alumino-3,3-diphenyl-propenes, whose proportions varied with the Lewis base present; and 1,1-diphenyl-1,3-butadiene gave a mixture of 4-alumino- and 3-alumino-1,1-diphenyl-1-butenes, together with 1-alumino-1,1-diphenyl-2-butene, whose composition was subject to both kinetic and thermodynamic control. Both the vinylsilanes gave a 70 30 mixture of the 1-silyl-1-alumino- and 1-silyl-2-alumino-ethanes with diisobutylaluminum hydride. When triethyl(vinyl)silane was heated with one-third mole of triisobutylaluminum, the ratio of 1- and 2-aluminoethanes fell to 18 82 . Finally, acenaphthylene underwent smooth hydralumination to yield 1-acenaphthyl-(diisobutyl)aluminum. Protolysis yielded varying amounts of acenaphthene and its ring protonated isomer, while carbonation yielded only acenaphthene-3-carboxylic acid. These results show that, in the absence of adverse steric factors, pπ- and dπ-conjugation favor the internal attachment of aluminum in hydralumination. Moreover, in cases where allylic aluminum systems result, the aluminum seems to prefer attachment to the site of highest electron density in the hypothetical anion R." @default.
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- W2085909175 date "1974-01-21" @default.
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- W2085909175 title "Organometallic compounds of group III XIVV. Orientation in the hydralumination of conjugated olefin hydrocarbons. Behavior of allylic organoaluminum systems" @default.
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- W2085909175 doi "https://doi.org/10.1016/s0022-328x(00)84254-0" @default.
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