
%0 Journal Article
%A Collins, DJ 
%A Hobbs, JJ 
%T Reactions of some carbanions generated with lithium aluminium hydride
%J Australian Journal of Chemistry
%D 1974/08/01
%V 27
%N 8
%P 1731-1741
%K 
%R https://doi.org/10.1071/CH9741731
%U https://www.publish.csiro.au/paper/CH9741731 
%X 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 &#945;,&#945;? -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. 
