springer.com Chemistry : Organic Chemistry Akhrem, A. A. Birch Reduction of Aromatic Compounds 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 Springer [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) . Softcover reprint of the 1st (NH:,) Q H H Ii Ij H H H H H+ X/~H M,l original 1st ed. 1972, VI, edition 126 p. Order online at springer.com/booksellers Springer Nature Customer Service Center GmbH Printed book Customer Service Softcover Tiergartenstrasse 15-17 69121 Heidelberg Printed book Germany Softcover T: +49 (0)6221 345-4301 ISBN 978-1-4757-0431-0 [email protected] £ 89,99 | CHF 118,00 | 99,99 € | 109,99 € (A) | 106,99 € (D) Available Discount group Science (SC) Product category Contributed volume Other renditions Softcover ISBN 978-1-4757-0430-3 Prices and other details are subject to change without notice. All errors and omissions excepted. Americas: Tax will be added where applicable. Canadian residents please add PST, QST or GST. Please add $5.00 for shipping one book and $ 1.00 for each additional book. Outside the US and Canada add $ 10.00 for first book, $5.00 for each additional book. If an order cannot be fulfilled within 90 days, payment will be refunded upon request. Prices are payable in US currency or its equivalent. ISBN 978-1-4757-0431-0 / BIC: PNN / SPRINGER NATURE: SCC19007 Part of .