Chapter 19-4 - CHEM 262 Wei You Chapter 19 Enolate Anions(4...

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11 CHEM 262 Wei You Chapter 19. Enolate Anions (4)
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22 Michael Reaction Michael reaction: the nucleophilic addition of an enolate anion to an α , β - unsaturated carbonyl compound Example: COOEt EtOOC O Et O -   Na + EtOH COOEt EtOOC O + 3-Buten-2-one (Methyl vinyl ketone) Diethyl propanedioate (Diethyl malonate)
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33 Michael Reaction CH 2 =CHCCH 3 O CH 2 =CHCOEt O CH 2 =CHCNH 2 O CH 3 CCH 2 CCH 3 O O CH 2 =CHNO 2 CH 2 =CHC N CH 2 =CHCH O CH 3 CCH 2 COEt O O O EtOCCH 2 COEt O N CH 3 C=CH 2 CH 3 CCH 2 CN O NH 3 , RNH 2 , R 2 NH These Types of  α,β -Unsaturated  Compounds are Nucleophile  Acceptors in Michael Reactions These Types of Compounds Provide Effective Nucleophiles for Michael Reactions β -Ketoester β -Diketone β -Diester Enamine β -Ketonitrile Aldehyde Ketone Ester Amide Nitrile Nitro compound Amine
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44 Michael Reaction COOEt O O EtO Na + EtOH O COOEt O 2-Cyclohexenone Ethyl 3-oxobutanoate (Ethyl acetoacetate) + O O + O + Example: the double bond of an α , β -unsaturated carbonyl compound is activated for nucleophilic attack
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