Wohl-Ziegler Reaction

Schematic representation of the Wohl-Ziegler Reaction.
Mechanism of the Wohl-Ziegler Reaction
Mechanism of the Wohl-Ziegler Reaction
Original publication
Ber. Dtsch. Chem. Ges.. 1919, 52, 51.
Review
Chem. Rev.. 1948, 43, 271.
Sample reactions
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intermediate structure
NBS
CCl4
intermediate structure
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intermediate structure
NBS
hν
CCl4
10 °C, 3 h
intermediate structure intermediate structure intermediate structure
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intermediate structure
CuBr, BzOOt-Bu
Dark
MeCN
-23 to 50 °C, 14 h, 62%
"Also isolated was the desired exocyclic allylic bromide (15 % yield, see next step)."
intermediate structure
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intermediate structure
Bz2O2, NBS
CCl4
Reflux, 6 h, 71%
intermediate structure
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intermediate structure
Bz2O2, NBS
CCl4
intermediate structure
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intermediate structure
AIBN, NBS
CCl4
Reflux, 2 h, 95%
intermediate structure
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intermediate structure
Bz2O2, NBS
CCl4
Reflux
intermediate structure
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intermediate structure
Br2
hν
CCl4
RT, 20 min, 63%
intermediate structure
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intermediate structure
Br2
hν
CCl4
RT, 2 h
intermediate structure
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intermediate structure
Br2
hν
CCl4
Reflux, 3.5 h
intermediate structure
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intermediate structure
Br2
hν
CCl4
Reflux, 30 min, 93%
intermediate structure
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intermediate structure
Br2
hν
CCl4
Reflux, , 96%
intermediate structure
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intermediate structure
AIBN, NBS
CCl4
Reflux, 3 h, 78%
intermediate structure
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intermediate structure
NBS
CCl4
Reflux, 12 h, 92%
"The starting material is obtained in 5 steps from acenaphthene, see: Chem. Ber. 1963, 96, 1098."
intermediate structure
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intermediate structure
Bz2O2, NBS
hν
CCl4
Reflux, 15 h, 100%
intermediate structure
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intermediate structure
AIBN, NBS
CCl4
Reflux, 45 min, 77%
intermediate structure
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intermediate structure
NBS
CCl4
Reflux, 3 h, 90%
intermediate structure
info
intermediate structure
Bz2O2, NBS
CCl4
Reflux, 3 h, 87%
intermediate structure
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intermediate structure
AIBN, NBS
hv
CCl4
65 °C, 2 h
intermediate structure