Reduction of diarylphthalides with aluminum lithium hydride

Conclusions The reduction of diarylphthalides with LiA1H₄ in THF leads to the corresponding diarylphthalans.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, p. 686, March, 1979.     

Silicon tetrafluoride : Preparation and reduction with lithium aluminium hydride

Pure silicon tetrafluoride can be prepared in 66% yield from silicon tetrachloride by refluxing with lead fluoride in acetonitrile. The gas can be reduced to pure silane by lithium aluminum hydride in diethyl ether.     

Reduction of unsaturated adamantyl-containing nitriles with lithium aluminum hydride in 2-methyltetrahydrofuran

Reduction of unsaturated adamantyl-containing nitriles with lithium aluminum hydride in 2-methyltetrahydrofuran was examined. It was found that under the synthesis conditions a simultaneous reduction of the double bond and the nitrile group successfully occurred. The presence of bulky substituents in the α-position to the adamantyl moiety of nitriles led to a significant increase in the synthesis duration. A satisfactory yield of the target compounds was achieved only by increasing the temperature and using a two-fold excess of lithium aluminum hydride.     

The lithium aluminium hydride reduction of cyclohexadienylmanganese complexes

Reduction of cyclohexadienyltricarbonylmanganese or its ring-substituted derivatives with lithium aluminium hydride leads to dihydro-derivatives. Preparative and NMR spectral information is presented and interpreted on the basis of the CH-bridged cyclohexenyl structure recently established for these products by Lamanna and Brookhart [3].     

Cyclopropane derivatives from the lithium aluminium hydride reduction of methoxyalkynols

Lithium aluminium hydride reduction of methoxyalkynol(1) yields cyclopropane derivatives (2) and (3), both formed by loss of a methoxy group; a reaction scheme for their formation is presented.     

Reduction of 1,2-diaroyl-1,2-diazetidines by lithium aluminum hydride

Reaction of a series of four-membered ring hydrazides (1,2-diaroyl-1,2-diazetidines) with lithium aluminum hydride at 80° results in reductive saturation of both carbonyl groups affording 1,2-diaryl-1,2-diazetidines in modest yield. Reactions at 22° result in reductive fragmentation at one carbonyl moiety, producing a monoaroyl-1,2-diazetidine as the exclusive product. A mechanism similar to that postulated for the temperature-dependent reduction of amides by lithium aluminum hydride is proposed for the reduction of these 1,2-diazetidines.     

Reduction of 4-hydroxy-3, 5-di-tert-butylphenylalkyl ketones with lithium aluminum hydride

Conclusions A new method was proposed for synthesizing 4-alkyl-2,6-di-tert-butylphenols by the reduction 4-hydroxy-3, 5-di-tert-butylphenyl ketones with lithium aluminum hydride.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 409–411,February, 1967.The authors would like to thank N. M. É manuél' for his constant interest in this work during its performance.     

Reduction of Z-2-chlorostilbene with lithium aluminum hydride: evidence for an electron transfer radical mechanism

$\text{Z}$-2-Chlorostilbene undergoes uncatalyzed LiAlH₄ reduction giving phenanthrene and $\text{Z}$-stilbene. An electron transfer radical mechanism is proposed. LiAlH₄ induced isomerization of $\text{Z}$-stilbene produces $\text{E}$-stilbene.     

Selective reduction. Reaction of 3,4-dicarbomethoxyquinoline with lithium aluminium hydride. Steric effect.

The selective reduction of 3,4-dicarbomethoxyquinoline by lithium aluminium hydride at low temperature affords only the unexpected 3-formyl 4-carbomethoxy quinoline. The difficulty of reduction of the usually more reactive 4-ester group can be explained by a steric hindrance by the H₅, peri proton on one side and by the 3-ester group on the other side.     

The reduction of 6-methoxy-9-methyl-11-oxoechiboline using lithium aluminium hydride

Reduction of 6-methoxy-9-methyl-11-oxoechiboline 1a using lithium aluminium hydride in boiling tetrahydrofuran under reflux affords 6-methoxy-9-methylechiboline. However, attempts to effect a similar reduction of a suspension of compound 1a in boiling diethyl ether under reflux, in which it is only very slightly soluble, were unsuccessful and when, under these conditions, a Soxhlet apparatus was employed to effect dissolution, an unexpected reductive ring scission occurred along with reduction of the carbonyl group to afford 4a-(2-aminoethyl)-6-methoxy-9-methyl-1,2,3,4,4a,9a-hexahydrocarbazole 3 .     

Metalation of 1-R-2-benzyl-o-carboranes with lithium aluminum hydride

Carboranes with the general formula I-R-2-PhCH₂-1,2-C₂B₁₀H₁₀ (R = Me, Prⁱ, Ph, PhCH₂) are readily metalated with lithium aluminum hydride in a THF solution at the CH₂ group. In this case only one hydrogen atom in LiAlH₄ is substituted, and trihydride complexes 1-R-2-PhCH(AlH₃Li)-1,2-C₂B₁₀H₁₀, are formed, which are stable in a solutionTranslated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1282–1284, May, 1996.