10.1002/ejoc.201701521
European Journal of Organic Chemistry
FULL PAPER
[2-(1-methoxy-1-methylethyl)phenyl]
(2,4,6-Trimethoxyphenyl)
Heterocycles 2015, 90, 631-644; f) T. Kitamura, K. Muta, J. Oyamada,
J. Org. Chem. 2015, 80, 10431-10438.
iodonium trifluoroacetate (17): 1,3,5-Trimethoxybenzene (16.8 mg, 0.1
mmol, 1.00 eq.) was added to a solution of 8a (40.6 mg, 0.1 mmol, 1.00
eq.) in CF3CH2OH. The reaction mixture was stirred at room temperature
for 24 hours. The mixture was evaporated under reduced pressure and
the crude oil was decanted with diethyl ether several times at room
temperature and then dried in vacuum to afford 17 (47.8 mg, 86 %).
Physical state: Colorless solid. m.p: 171.8-174.0 °C. 1H NMR (500 MHz,
CDCl3): 7.37-7.43 (m, 2 H), 7.12-7.15 (td, J = 7.4, 1.7 Hz 1H), 6.98 (d, J
= 8.0 Hz, 1 H), 6.26 (s, 2 H), 3.91 (s, 3 H), 3.86 (s, 6 H), 3.57 (s, 3 H),
1.67 (s, 6 H). 13C NMR (125 MHz, CDCl3): 167.2, 161.1, 160.9 (q, J =
32.4 Hz), 145.4, 130.3, 130.2, 129.3, 128.1, 117.0 (q, J = 296.3 Hz),
110.4, 91.6, 84.8, 79.2, 56.93, 56.91, 55.91, 55.89, 50.0, 25.4. 19F NMR
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Keywords: iodosylbenzene • trifluoroacetic acid • pseudocyclic •
coordination • oxidation
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