Chapter 18: Enols and Enolates
Conjugate Addition reactions
Summary
Conjugate
or 1,4-addition tends to occur with nucleophiles that are weaker bases.
Examples : thiols
RSH
, cyanide ion
-
CN
, organocopper reagents
R
2
CuLi
, and enolates.
Direct
or 1,2-addition tedns to occur with nucleophiles that are stronger bases.
Examples : Organolithiums
RLi
, lithium aluminium hydride,
LiAlH
4
and Grignard reagents,
RMgX
.
The product of conjugate addition is usually more stable (
i.e.
the thermodynamic product) as it still contains the strong
C=O
bond.
Organocuprates
Michael reaction
©
Dr. Ian Hunt
, Department of Chemistry