D
Z. Yang et al.
Letter
Synlett
COOH
Fe(NO3)3
COOFe(NO3)2
path 1
Fe(NO3)2
path 2
– CO2
a
b
NO2
NO2
COOFe(NO3)2
NO2
Fe(NO3)2
NO2
d
c
NO2
– CO2
Scheme 3 Proposed mechanism for the decarboxylative nitration process
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(14) Procedure for the Synthesis of β-Nitrostyrene
The mixture of cinnamic acid (0.5 mmol), Fe(NO3)3 (1.0 mmol),
pyridine (0.5 mmol), and toluene (2 mL) was stirred at 100 °C
for 12 h. After cooling to r.t., the reaction mixture was washed
with H2O (10 mL) and extracted by EtOAc (3×). The organic
phase was dried with anhydrous MgSO4. The mixture was con-
centrated in vacuo, and the residue was purified by column
chromatography on silica gel (15% EtOAc–n-hexane) to afford
pure product.
Yellow solid (90%, 77 mg). 1H NMR (400 MHz, CDCl3): δ = 7.37–
7.57 (m, 5 H), 7.59 (d, J = 13.7 Hz, 1 H), 8.01 (d, J = 13.7 Hz, 1 H).
13C NMR (100 MHz, CDCl3): δ =129.16, 129.43, 130.14, 132.15,
137.19, 139.06.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–D