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SmI 2 causes reductive dimerization of allylic or benzylic halides, and chiral halides undergo non-stereospecific reduction. [5] On the other hand, its functional group compatibility is greater than many reducing agents—halide reduction is possible in the presence of esters or alcohols. [6]
In addition to the reduction of metal halides, the reagents associated with this methodology are applicable to deoxygenation of organic substrates. [1] A typical reducing agent is N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene. Related pyrazine- and cyclohexadiene-based reagents have been developed. They are red or orange THF-soluble solids.
One-electron reducing agents, such as d 6 or d 1 transition metal complexes, initially donate a single electron to the halo ketone. Fragmentation of the resulting radical anion yields an organic radical and halide anion. Donation of a second electron from a second equivalent of reducing agent leads to the formation of a metal enolate in which ...
The result of these trends is that acid halides, ketones, and aldehydes are usually the most readily reduced compounds, while acids and esters require stronger reducing agents. Importantly and characteristically, these hydride reagents generally do not attack C=C bonds. [2] Several factors contribute to the strength of metal hydride reducing ...
Hydrogen gas is a reducing agent when it reacts with non-metals and an oxidizing agent when it reacts with metals. 2 Li (s) + H 2(g) → 2 LiH (s) [ a ] Hydrogen (whose reduction potential is 0.0) acts as an oxidizing agent because it accepts an electron donation from the reducing agent lithium (whose reduction potential is -3.04), which causes ...
Lithium aluminium hydride also reduces alkyl halides to alkanes. [36] [37] Alkyl iodides react the fastest, followed by alkyl bromides and then alkyl chlorides. Primary halides are the most reactive followed by secondary halides. Tertiary halides react only in certain cases. [38] Lithium aluminium hydride does not reduce simple alkenes or arenes.
Egorov and his co-workers have reported dehalogenation of benzyl halides using atomic magnesium in 3P state at 600 °C. Toluene and bi-benzyls were produced as the product of the reaction. [9] Morrison and his co-workers also reported dehalogenation of organic halides by flash vacuum pyrolysis using magnesium. [10]
Sodium borohydride and lithium aluminium hydride are commonly used for the reduction of organic compounds. [3] [4] These two reagents are on the extremes of reactivity—whereas lithium aluminium hydride reacts with nearly all reducible functional groups, sodium borohydride reacts with a much more limited range of functional groups.