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- W2075406475 startingPage "3783" @default.
- W2075406475 abstract "The hydroalumination of a terminal allene, 1,2-nonadiene, with LiAlH4 in THF using [TiCl2(Cp)2], TiCl4, TiCl3, ZrCl4, and [ZrCl2(Cp)2] catalysts afforded a wide variety of deuterated species by quenching hydroalumination products with D2O, while PhB(OH)2-catalyzed hydroalumination with AlHCl2 in ether gave >95% pure 1-nonene-3-d as predominant product (92%) in high yield. The allylation of benzaldehyde using the PhB(OH)2-catalyzed hydroalumination product suggested that the resulting hydroalumination product may be the allylaluminum compound, 2-nonenylaluminum dichloride. Allylation of trans-cinnamaldehyde using this allylaluminum compound proceeded with high regioselectivity, leaving the ketone functionality intact. Allylative ring-opening reaction of epoxides was less regioselective. The combination of catalytic PhB(OH)2 with AlHCl2 also was effective for the regioselective hydroalumination of the disubstituted allenes, vinylidenecyclohexane and 1-trimethylsilyl-1,2-nonadiene, although the trisubstituted allene, 1-butenylidenecyclohexane, showed nonregioselective orientation results." @default.
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- W2075406475 date "1993-12-01" @default.
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- W2075406475 title "Regioselective Hydroalumination of Allenes and Their Synthetic Application" @default.
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- W2075406475 doi "https://doi.org/10.1246/bcsj.66.3783" @default.
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