NUCLEOPHILIC ADDITION TO CONJUGATED SYSTEMS: CONJUGATE ADDITION AND MICHAEL REACTIONS
401
CN
OMe
O
Nu
CN
OMe
O
Nu
C
OMe
O
Nu
OMe
O
Nu
OMe
O
Nu
OMe
O
Nu
N
C
OMe
O
Nu
N
methyl methacrylate
methyl cyanoacrylate
CO 2 Me
C
C
Nu
C
Nu
acrylonitrile
CN
N
N
N
CO 2 Me
NC
polyacrylonitrile
poly(methyl methacrylate)
poly(methyl cyanoacrylate)
superglue
Nu
OMe
O
C
N
CN
OMe
O
CN
OMe
O
Nu
Methyl cyanoacrylate combines the anion-stabilizing features of both an ester group and a nitrile. Addition
anions form very easily because of their enhanced resonance stability, and this polymerization process forms the
basis of superglue. Traces of moisture on surfaces (including fingers) initiate anionic polymerization and the
bonding together of almost any materials. Superglue now has some value in surgery, bonding tissue without the
need for stitches.
401
CN
OMe
O
Nu
CN
OMe
O
Nu
C
OMe
O
Nu
OMe
O
Nu
OMe
O
Nu
OMe
O
Nu
N
C
OMe
O
Nu
N
methyl methacrylate
methyl cyanoacrylate
CO 2 Me
C
C
Nu
C
Nu
acrylonitrile
CN
N
N
N
CO 2 Me
NC
polyacrylonitrile
poly(methyl methacrylate)
poly(methyl cyanoacrylate)
superglue
Nu
OMe
O
C
N
CN
OMe
O
CN
OMe
O
Nu
Methyl cyanoacrylate combines the anion-stabilizing features of both an ester group and a nitrile. Addition
anions form very easily because of their enhanced resonance stability, and this polymerization process forms the
basis of superglue. Traces of moisture on surfaces (including fingers) initiate anionic polymerization and the
bonding together of almost any materials. Superglue now has some value in surgery, bonding tissue without the
need for stitches.