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- W1566205541 abstract "Reduction (80°) and reductive methylation (160–175°) of some geminal diphenyl-substituted olefins and conjugated dienes by sodium bis(2-methoxyethoxy)aluminium hydride are described. 1,1-Diphenylethylene was reduced to give 1,1-diphenylethane as a sole product, while reductive methylation gave 2,2-diphenylpropane in high yield. Similarly, 1,2,2-triphenylpropane was obtained from 1,1,2-triphenylethylene. Reductive methylation of cyclohexylidene diphenylmethane took place with partial rearrangement of the exocyclic double bond to give 1-(1-cyclohexenyl)-1,1-diphenylethane as the main product, which was accompanied by cyclohexyldiphenylmethane and 1-cyclohexyl-1,1-diphenylethane. 1,1,4,4-Tetraphenyl-1,3-butadiene at 175° underwent a new type of a reductive C—C bond cleavage leading to a 88/12 mixture of 2,2-diphenylpropane and 2,2-diphenylbutane, both formed by methylation of cleavage fragments. The reduction of 6,6-diphenylfulvene afforded a mixture of isomers, which from the NMR and mass spectra, were identified as 1-(diphenylmethyl)-1,3-cyclopentadiene (47%), 2-(diphenylmethyl)-1,3-cyclopentadiene (47%) and 5-(diphenylmethyl)-1,3-cyclopentadiene (6%). Reductive methylation of this mixture or of 6,6-diphenylfulvene alone gave a mixture of 1-(1,3-cyclopentadien-1-yl)-1,1-diphenylethane, 1-(1,3-cyclopentadien-2-yl)-1,1-diphenylethane and 1-(1,3-cyclopentadien-5-yl)-1,1-diphenylethane in a similar ratio. When 9-hydroxy-9-methylfluorene was used in place of biphenylene ethylene, hydrogenolytic methylation by the hydride afforded 9,9-dimethylfluorene in high yield. In all cases the methylation reaction is regioselective, and takes place exclusively at the phenyl-activated benzylic carbon atom of acidic hydrocarbons." @default.
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- W1566205541 date "1975-01-01" @default.
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- W1566205541 title "Reaction of sodium bis(2-alkoxyethoxy)aluminium hydrides" @default.
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- W1566205541 doi "https://doi.org/10.1016/s0022-328x(00)90027-5" @default.
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