Birch Reduction of Aromatic Compounds by Aa Akhrem

Birch Reduction of Aromatic Compounds by Aa Akhrem

Birch reduction (see reviews [1-5]) is the name given to the reaction of unsaturated organic compounds with alkali metals and alcohols in liquid am- monia. 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 and broad application of this reaction was achieved only after a series of investigations by Birch published from 1944 onwards [7J. Since the presence of an alcohol in the reaction medium is not indispen- sable for pOlycyclic aromatic systems, the present review includes only deriv- atives of the simplest aromatic compounds - benzene and naphthalene. 1 Reaction Mechanism The most probable mechanism of Birch reduction, adopted by the major- ity of 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

SKU	Unavailable
ISBN 13	9780306651588
ISBN 10	0306651580
Title	Birch Reduction of Aromatic Compounds
Author	Aa Akhrem
Condition	Unavailable
Binding Type	Hardback
Publisher	Springer Science+Business Media
Year published	1972-01-01
Number of pages	132
Cover note	Book picture is for illustrative purposes only, actual binding, cover or edition may vary.