Diels alder reaction

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Diels-Alder Reaction

ORGANIC CHEMISTRYCYCLIC ADDITION DIELS ALDER REACTION PROF.DR . NAZ M ATABAY DEPARTMENT OF CHEMISTRY FATIH UNIVERSITY MSc.student . NABEEL B AZEEZ OUTLINES INTRODUCTIONTHE REACTION REACTION MECHANISMSTEREOSELECTIVITYRETROSYNTHETIC ANALYSISRECENT LITERATURE REFRENCES

Diels-Alder Reaction

Otto DielsKurt Alder

1950.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. INTRODUCTION

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 -systems, such ascarbonylsandimines, to furnish the corresponding heterocyclic, known as thehetero-DielsAlder reaction. DielsAlder reactions can be reversible under certain conditions; the reverse reaction is known as theretro-DielsAlder reaction.

conjugateddienedienophilecyclohexeneDIELS ALDER REACTIONbetween a conjugateddieneand a substitutedalkene, commonly termed the dienophile, to form a substitutedcyclohexenesystemTHE MECHANISM

A conjugated diene reacts with a double-bonded dienophile

THE MECHANISM

Normally, dienes are electron-rich; dienophiles are electron-poor

THE MECHANISM Normally, dienes are electron-rich; dienophiles are electron-poor

DielsAlder reactions, as concerted cycloadditions, are tereospecific, i.e. stereo chemical information in the reactants is retained in the products.E- andZ-dienophiles, for example, give rise to the adducts with correspondingsynoranti-stereochemistry STEREOSELECTIVITY

STEREOSELECTIVITY

Retro synthetic analysis using theDiels-Alder reaction

RECENT LITERATURE

* 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.ukReferences