Diels alder reaction

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. Diels-Alder Reaction                                  Otto Diels Kurt Alder 1950

4. . 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

5. 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 DIELS – ALDER REACTION between a conjugated  diene  and a substituted  alkene , commonly termed the dienophile , to form a substituted  cyclohexene  system

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

9. 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 STEREOSELECTIVITY

10. STEREOSELECTIVITY

11. Retro synthetic analysis using the Diels-Alder reaction

12. RECENT LITERATURE

13. * 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 References