diels alder reaction
TRANSCRIPT
PROF.DR . NAZ M ATABAY
DEPARTMENT OF CHEMISTRY
FATIH UNIVERSITY
MSc.student . NABEEL B AZEEZ
INTRODUCTIONTHE REACTION REACTION MECHANISMSTEREOSELECTIVITYRETROSYNTHETIC ANALYSIS
RECENT LITERATURE
REFRENCES
Diels-Alder Reaction
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Otto Diels Kurt Alder
• .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.
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The Diels–Alder 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 π-systems, such as carbonyls and imines, to
furnish the corresponding heterocyclic, known as the hetero-Diels–Alder
reaction. Diels–Alder reactions can be reversible under certain conditions;
the reverse reaction is known as the retro-Diels–Alder reaction.
conjugated diene dienophile cyclohexene
between a conjugated diene and a substituted alkene, commonly
termed the dienophile, to form a substituted cyclohexene system
A conjugated diene reacts with a double-bonded dienophile
Normally, dienes are electron-rich; dienophiles are electron-poor
Normally, dienes are electron-rich; dienophiles are electron-poor
Diels–Alder 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
Retro synthetic analysis using theDiels-Alder reaction
* 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/namedreactions/diels-alder-reaction.shtm
* Wikipedia.co.uk