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Bn
Bn
Cl
N
O
N
O
N
N
1. ClCO
2
Et
2. KOH, H
2
NNH
2
HOCH
2
CH
2
OH
NCS
AlH
3
H
N
N
H
O
2
i
-Pr
2
NEt
2APLY
Scheme 3.7
Synthetic method for
2APLY
coefficients of the SOMO, perturbations on their electronic structures are expected to be much smaller
than those of
-type
APLY
s.
The synthetic method for
2APLY
isshowninScheme3.7.
33
Reduction of the carbonyl groups of the
1,8-naphthalimide derivative and the following deprotection of the benzyl group give the amine derivative.
N
-Chlorination, dehydrochlorination and oxidation with oxygen give
2APLY
as a yellow - green solution.
While this neutral radical is stable in a degassed solution for months, the radical stability with air in the
solution and in the solid state is low, hampering its isolation as a pure form.
α
N
CH(OEt)
3
H
2
NCONH
2
EtO
2
C
CO
2
Et
EtO
2
C
CO
2
Et
O
O
POCl
3
N
N
CH
2
(CN)
2
KH
EtO
2
C
CO
2
Et
EtO
2
C
CO
2
Et
Cl
NC
CN
Cl
Cl
Cl
N
Cl
Cl
Cl
Cl
N
Cl
Cl
N
PCl
5
Me
4
NCl
Cl
Cl
Cl
N
Bu
4
NI
N
Cl
Cl
Cl
+
N
Cl
N
N
N
N
N
Cl
N
Cl
Cl
Cl
Cl
Cl
Cl
PTAZ
Scheme 3.8
Synthesis of
PTAZ
and the dechlorinated closed shell dimer
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