Chemistry Reference
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N
N
Ar
N
Ar
Ar
N
N
N
(1.20)
1)
n
-BuLi
2) I
2
N
N
N
•
N
N
N
Ph
Ar
Ph
Ph
63
64
65
X
Ar
1
Ar
1
Ar
1
N
Ar
1
N
N
1)
n
-BuLI
2) I
2
3) H
2
O
N
N
X
N
N
C
•
N
N
+
Ar
Ar
Ar
N
(1.21)
N
N
N
Ar
67
68
66
69
X
X
X
−
N
2
Ar
Ar
Ar
•
(1.22)
N
N
N
N
•
N
67
70
69
N
N
N
N
N
N
+
•
(1.23)
N
N
N
N
71
72
73
1.9 Delocalized persistent radicals: analogues of triarylmethyl radicals
The discovery by Gomberg of the triphenylmethyl radical opened the way for the discovery of a variety
of related persistent radicals. Some of these are covered in greater detail elsewhere in this topic. Schlenk
and Mark reported the preparation of the equilibrating pentaphenylethyl radical
74
,
25a
which exists as a
long lived species (Equation 1.24). Karl Ziegler and coworkers prepared the tetraphenylallyl radical
75
25b
and the pentaphenylcyclopentadienyl radical
76
.
25c
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