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.     

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.     

Reactions of phenyllithium with lithium aluminum hydride in diethyl ether

Reactions of phenyllithium with LiAlH₄ in diethyl ether have been studied in detail. Lithium hydride, as an insoluble solid, and LiAlPh_n H_4?n (where n = 2 or 3)_in solution, are formed when the PhLi to LiAlH₄ ratio is 2/1and 3/1. However, Li₃AlH₆ is formed when LiAlH₄ is added to an equimolar solution of PhLi in diethyl ether. The integrity of the products have been established by IR, NMR and X-ray powder diffraction pattern.     

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.     

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 aryl bromides with lithium aluminum hydride: Evidence for a radical mechanism

Reduction of $\text{0}$-bromophenyl allyl ether with LiAlH₄ yields phenyl allyl ether and 3-methyl-2,3-dihydrobenzofuran, thus suggesting the involvement of radical intermediates in the reduction.     

Reductions of acetylenes and conjugated diolefins by lithium aluminum hydride

A convenient method is described for the stereospecific reduction of acetylenes by LAH. For example, 2-pentyne, 3-hexyne, 1-phenylpropyne and diphenylethyne in an ether solvent have been reduced to the corresponding trans olefin in high yield 2,4-Hexadiene was reduced in a similar manner to give a mixture of 2- and 3-hexenes. With toluene as the solvent, the main products from acetylenes are the saturated hydrocarbons. Whereas a trans addition of the hydride to the triple bond occurs in ether solvents, it appears that cis addition occurs in toluene.