The Birch reduction in organic synthesis

@article{Birch1996TheBR,
  title={The Birch reduction in organic synthesis},
  author={Arthur J. Birch},
  journal={Pure and Applied Chemistry},
  year={1996},
  volume={68},
  pages={553 - 556}
}
  • A. Birch
  • Published 1996
  • Chemistry
  • Pure and Applied Chemistry
The unique availability of substituted cyclohaa-I, 4and 1,Edienes notably enol ethers, from Birch reduction of benzenes, permits many novel synthetic reactions of general utitility. Some principles are discussed. The Birch Reduction has greatly increased the utility of benzenoid compounds in alicyclic synthesis'. It has had a less profound effect on heterocyclic synthesis'. It provides steric control in many situations. It is one of the most highly used"' synthetic reactions in organic… Expand
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Paper Mentions

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References

SHOWING 1-6 OF 6 REFERENCES
"J."
however (for it was the literal soul of the life of the Redeemer, John xv. io), is the peculiar token of fellowship with the Redeemer. That love to God (what is meant here is not God’s love to men)Expand
Faraday Discussion: The M i l e Molecule, 1947 J
  • Chem. Soc.,
  • 1950
and Uma Javed SheriffJ
  • Chem. Soc., Perkin Trans. I,
  • 1991
Current Science, Indiu, 1982, 51, 155
  • Progress in Molecular Biology Ad. Yu.A. Orchinnikov Elsevier N.Y.
  • 1984
Aust
  • J. Chem.,
  • 1969
Aust
  • J. Chem., 1955, 8, 96 A.J. Birch, D.N. Butler, C.J. Moye, R.W. Richards, J.B. Siddall Bull. Nut. Inst. Sci. India,
  • 1965