Birch Reduction of Aromatic Compounds

Authors: Akhrem, A. A.

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About this book

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

Table of contents (6 chapters)

Buy this book

eBook $89.00
price for USA in USD (gross)
  • ISBN 978-1-4757-0429-7
  • Digitally watermarked, DRM-free
  • Included format: PDF
  • ebooks can be used on all reading devices
  • Immediate eBook download after purchase
Softcover $119.99
price for USA in USD
  • ISBN 978-1-4757-0431-0
  • Free shipping for individuals worldwide
  • Usually dispatched within 3 to 5 business days.
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Bibliographic Information

Bibliographic Information
Book Title
Birch Reduction of Aromatic Compounds
Authors
Copyright
1972
Publisher
Springer US
Copyright Holder
Springer Science+Business Media New York
eBook ISBN
978-1-4757-0429-7
DOI
10.1007/978-1-4757-0429-7
Softcover ISBN
978-1-4757-0431-0
Edition Number
1
Number of Pages
VI, 126
Topics