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Title: diels - alder reaction


1
ORGANIC CHEMISTRY
CYCLIC ADDITION DIELS ALDER REACTION
PROF.DR . NAZ M ATABAY DEPARTMENT OF CHEMISTRY
FATIH UNIVERSITY
MSc.student . NABEEL B AZEEZ
2
OUTLINES
  • INTRODUCTION
  • THE REACTION
  • REACTION MECHANISM
  • STEREOSELECTIVITY
  • RETROSYNTHETIC ANALYSIS
  • RECENT LITERATURE
  • REFRENCES

3
1950
Kurt Alder
Otto Diels
Diels-Alder Reaction
4
INTRODUCTION
  • diene synthesis has developed into one of the
    most important working methods in organic
    chemistry .
  • The method has also proved valuable in a great
    many ways in research into the constitution of
    complex natural products .
  • formed by diene synthesis are usually stable.

5
DIELS ALDER REACTION
The reaction is taken place between a
conjugated diene and a substituted alkene,
commonly termed the dienophile, to form a
substituted cyclohexene system
conjugated diene
cyclohexene
dienophile
The DielsAlder reaction is particularly useful
in synthetic organic chemistry as a reliable
method for forming 6-membered systems with good
control over regio- and stereo chemical
properties. The underlying concept has also been
applied to other p-systems, such
as carbonyls and imines, to furnish the
corresponding heterocyclic, known as
the hetero-DielsAlder reaction. DielsAlder
reactions can be reversible under certain
conditions the reverse reaction is known as
the retro-DielsAlder reaction.
6
THE MECHANISM
A conjugated diene reacts with a double-bonded
dienophile
7
THE MECHANISM
Normally, dienes are electron-rich dienophiles
are electron-poor
8
THE MECHANISM
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STEREOSELECTIVITY
  • DielsAlder reactions, as concerted
    cycloadditions, are tereospecific, i.e. stereo
    chemical information in the reactants is retained
    in the products. E- and Z-dienophiles, for
    example, give rise to the adducts with
    corresponding syn or anti-stereochemistry

12
STEREOSELECTIVITY
13
Retro synthetic analysis using the Diels-Alder
reaction
14
RECENT LITERATURE
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References
  • Organic chemistry Clayden, J. Greeves, N.
    Warren, S. Wothers, P. Oxford University Press,
    Oxford, 2006.
  • Lewis Acids and Selectivity in Organic
    Synthesis Santelli, M. Pons, J. CRS Press, USA,
    1995. \ http//www.organic-chemistry.org/namedrea
    ctions/diels-alder-reaction.shtm
  • Wikipedia.co.uk

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