Chemistry Reference
In-Depth Information
Ph
R
R
H
Ph
Br
Br
, toluene
>90%
+
O
O
O
Ph
Br
Br
H
Ph
104
R
R
105
103
R = C
6
H
13
4:1
endo
:
exo
R
Ph
H
Ph
endo
105
O
O
O
106
1. DDQ, toluene
2. BuLi, furan
3. tetracyclone, EtOH
30%
Ph
1.5:1
endo-syn:endo-anti
H
R
Ph
R
Ph
H
Ph
exo
105
O
O
O
107
Ph
1:1
exo-syn:exo-anti
H
R
Ph
R
R
exo
H
H
H
O
O
O
107
, toluene
45%
R
R
H
H
H
p
-TsOH, toluene
47%
, toluene
25%
H
H
H
R
R
106
endo
O
O
O
H
H
H
R
R
R
108
109
Acid
R
R
R
110
Fig. 49 Schl¨ ter's synthesis of a buckybelt precursor [
76
]
R
R
OAc
R
R
mass spectrometry
(observed)
AcO
OAc
R
R
AcO
R
R
110
111
Fig. 50 Observation of a buckybelt under mass spectrometric conditions [
78
]
