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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions of some carbanions generated with lithium aluminium hydride

DJ Collins and JJ Hobbs

Australian Journal of Chemistry 27(8) 1731 - 1741
Published: 1974

Abstract

Treatment of erythro-2,3-bis(p-methoxyphenyl)butyronitrile with lithium aluminium hydride in tetrahydrofuran gave the stable 2-anion, protonation of which gave a 2.3 : 1 erythro : threo mixture of the nitrile; in air, 1,2-bis(p-methoxyphenyl)propan-1-ol was formed by oxygenation of the anion. The same anion was produced rapidly and quantitatively from 2,3-bis(p-methoxyphenyl)crotononitrile with LiAlH4 in tetrahydrofuran. Some reactions of carbanions generated similarly from α,α? -dicyanostilbene, 9-benzylidenefluorene, fluoren-9-ylidenemalononitrile and 1,l-diphenylethylene are described. 2,3-Bis(pmethoxyphenyl)butadiene was reduced with LiAlH4 in tetrahydrofuran to give a mixture of (Z)- and (E)-2,3-bis(p-methoxyphenyl)but-2-ene and 2,3-bis(p-methoxypheny1)but-l-ene, probably via organoaluminium intermediates.

https://doi.org/10.1071/CH9741731

© CSIRO 1974

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