Titlebook: Birch Reduction of Aromatic Compounds; A. A. Akhrem,I. G. Reshetova,Yu. A. Titov Book 1972 Springer Science+Business Media New York 1972 a

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Field of Application,stituents. In the first stage of the reaction, 1,4-dihydro derivatives are always formed and through the further reactions of these are effected transformations to various compounds frequently difficult of access by other methods of synthesis.

Chauvinistic

Methods and Examples of the Performance of the Reaction,f addition of the reagents — the alkali metal, the ammonia, and the alcohol — and also by the presence or absence of supplementary solvents. Since the reaction is carried out in liquid ammonia, its temperature range is determined by the boiling and solidification points of ammonia (from -34°C to -80°C).

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Introduction,uid ammonia in the presence of an alcohol, while this reaction does not take place in the absence of an alcohol. However, the general recognition and broad application of this reaction was achieved only after a series of investigations by Birch published from 1944 onwards [7].

Flu表流動

Review of Literature Information,e of complex reaction products, the structural formula is given only for that part of the molecule in which changes took place during Birch reduction. Tetrahydrofuran used as an auxiliary solvent is denoted in the table by THF.

姑姑在炫耀

Book 1972onia. This method was first used for aromatic compounds in 1937 by Wooster [6J, who showed that benzene and its derivatives are reduced by sodium in liq- uid ammonia in the presence of an alcohol, while this reaction does not take place in the absence of an alcohol. However, the general recognition

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Book 1972 workers in this field [4, 8 -12] can be represented by the following stages: ‘v I NH -‘" ,. - i T 1 3 +--"‘( a) , , ,e (NHa) NH 3) + ROH ----+ () ll. . (NHa) A H H 4) H H 5) ‘)‘, ",,\+ + RO" ~ Q + 110M,,,,,, / (NHa) . (NH:,) Q H H Ii Ij H H H H H+ X/~H M,l