Skip to main content
SpringerLink
Log in
Book cover
  • Book
  • © 1972

Birch Reduction of Aromatic Compounds

Authors:

  1. A. A. Akhrem

    1. Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, USSR

    View author publications

    You can also search for this author in PubMed   Google Scholar

  2. I. G. Reshetova

    1. Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, USSR

    View author publications

    You can also search for this author in PubMed   Google Scholar

  3. Yu. A. Titov

    1. Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, USSR

    View author publications

    You can also search for this author in PubMed   Google Scholar

Sections

Buy it now

eBook USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Other ways to access

This is a preview of subscription content, log in via an institution to check for access.

Table of contents (6 chapters)

  1. Front Matter

    Pages i-v
    PDF

  2. Introduction

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 1-1

  3. Reaction Mechanism

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 2-3

  4. Field of Application

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 4-7

  5. Side Reactions

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 8-14

  6. Methods and Examples of the Performance of the Reaction

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 15-17

  7. Review of Literature Information

    • A. A. Akhrem, I. G. Reshetova, Yu. A. Titov
    Pages 18-111

  8. Back Matter

    Pages 112-125
    PDF
Back to top

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
Back to top

Keywords

Back to top

Authors and Affiliations

  • Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow, USSR

    A. A. Akhrem, I. G. Reshetova, Yu. A. Titov

Back to top

Bibliographic Information

  • Book Title: Birch Reduction of Aromatic Compounds

  • Authors: A. A. Akhrem, I. G. Reshetova, Yu. A. Titov

  • DOI: https://doi.org/10.1007/978-1-4757-0429-7

  • Publisher: Springer New York, NY

  • eBook Packages: Springer Book Archive

  • Copyright Information: Springer Science+Business Media New York 1972

  • Softcover ISBN: 978-1-4757-0431-0Published: 12 December 2012

  • eBook ISBN: 978-1-4757-0429-7Published: 06 December 2012

  • Edition Number: 1

  • Number of Pages: VI, 126

  • Topics: Organic Chemistry

Back to top

Publish with us

Policies and ethics

Back to top
Access via your institution

Buy it now

eBook USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Other ways to access

Search

Navigation