126
4 Applications of Nitrile Imine Derivatives
polystyrene derivative. Employing an excess of 2,5-tetrazole enabled further surface modification of the resulting SCNP with a second dipolarophiles (Scheme 4.31)
[91]. A recent contribution replicated this chemistry with the inclusion of a diazo
moiety into the backbone of a polycarbonate scaffold. Following SCNP formation,
degradation of the polymer was induced through the introduction of a reducing agent
[92].
HO
O
N N
N
N
OMe
H2
C
H2
C C
H
H2
C C
H
H2
C C
H
C
H
n
C
H
Ph
C
H
H2
C
C
H
H2
C
Ph
C
H
H2
C
H2
C
n
Cs2CO3, DMF
40 °C, 48 h
C
H
C
H
H2
C
C
H
H2
C
H
C
H2
C
H2
C
n
H
C
H
C
H2
C
H
C
H2
C
H
C
H2
C
H2
C
n
h
THF
rt, 1 h
SCNP
SCNP
Ph
Cl
Cl
Cl
Cl
H2
C
H2
C C
H
H2
C C
H
H2
C C
H
C
H
n
H2
C
H2
C C
H
H2
C C
H
H2
C C
H
C
H
n
Ph
N
N
N
Ar
N
N
O
O
O
Ph
Ph
N
N
N
Ar
N
N
O
O
O
N
O
O
O
O
O
OH
O
O
O
Ph
Ph
Ph
Cl
N
N
N
Ar
N
N
N
Ar
N
Ar
N
N
O
O
O
N
N
Ar
N
O
O
O
C
H
C
H
H2
C
C
H
H2
C
H
C
H2
C
H2
C
n
H
C
H
C
H2
C
H
C
H2
C
H
C
H2
C
H2
C
n
Ph
Ph
Ph
N
N N
N
Ar
N
Ar
N
N
O
O
O
N
N
Ar
N
O
O
O
N
O
O
R 1
N
O
O
R 1
h
THF
rt, 1 h
+
h
h
Scheme 4.31 The application of intramolecular NI cycloaddition in the synthesis of SCNPs