The Journal of Organic Chemistry
Note
260.0658. These spectroscopic data correspond to previously reported
data.43
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4,4,4-Trifluoro-1-phenylbutane-1,3-dione (5r). This product was
isolated in enol form: white needle crystals; yield 98% (1.05 g); mp
35−37 °C; 1H NMR (400 MHz, CDCl3) δ 15.14 (br, 1H), 7.95 (t, J =
8.4 Hz, 2H), 7.52−7.65 (m, 3H), 6.58 (s, 1H); 13C NMR (100 MHz,
CDCl3) δ 186.3, 177.3 (q, J = 36.0 Hz), 134.2, 132.9, 129.1, 127.7,
117.4 (q, J = 281.0 Hz), 92.2; 19F NMR (376 MHz, CDCl3) δ −77.0.
These spectroscopic data correspond to previously reported data.44
2-(2,2,2-Trifluoroacetyl)-3,4-dihydro-2H-naphthalen-1-one (5s).
This product was isolated in enol form: white needle crystals; yield
98% (1.18 g); mp 49−50 °C; 1H NMR (400 MHz, CDCl3) δ 15.67 (s,
1H), 7.99 (d, J = 8.4 Hz, 1H), 7.50 (t, J = 8.4 Hz, 1H), 7.37 (t, J = 8.4
Hz, 1H), 7.27 (d, J = 8.4 Hz, 1H), 2.91 (t, J = 8.4 Hz, 2H), 2.76 (t, J =
8.4 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 182.1, 175.1 (q, J = 34.2
Hz), 141.8, 133.8, 129.7, 128.0, 127.3, 126.6, 118.0 (q, J = 283.0 Hz),
104.4, 27.7, 20.7; 19F NMR (376 MHz, CDCl3) δ −72.1. These
spectroscopic data correspond to previously reported data.45
1,1,1,2,2-Pentafluoro-5-phenylpentan-3-one (3p): colorless oil;
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1
yield 99% (1.25 g); H NMR (400 MHz, CDCl3) δ 7.17−7.32 (m,
5H), 3.07 (t, J = 8.0 Hz, 2H), 2.98 (t, J = 8.0 Hz, 2H); 13C NMR (100
MHz, CDCl3) δ 193.5 (q, J = 26.0 Hz), 139.4, 128.7, 128.3, 126.7,
117.9 (qt, J = 284.0, 33.0 Hz), 107.1 (tq, J = 265.0, 38.0 Hz), 39.1,
28.4; 19F NMR (376 MHz, CDCl3) δ −81.9, −123.3; HRMS (ESI) m/
z calcd for C11H9F5O 252.0574, found 252.0571. These spectroscopic
data correspond to previously reported data.46
1,1,1,2,2-Pentafluoro-5-(4-methoxycarbonyl)phenyl)pentan-3-
one (3q): colorless oil; yield 97% (1.50 g); 1H NMR (400 MHz,
CDCl3) δ 7.95 (d, J = 7.2 Hz, 2H), 7.25 (d, J = 7.2 Hz, 2H), 3.70 (s,
3H), 3.14 (t, J = 8.0 Hz, 2H), 3.01 (t, J = 8.0 Hz, 2H); 13C NMR (100
MHz, CDCl3) δ 193.2 (q, J = 27.0 Hz), 166.6, 144.6, 129.8, 128.6,
128.2, 117.8 (qt, J = 290.0, 34.0 Hz), 106.9 (tq, J = 270.0, 38.0 Hz),
51.7, 38.2, 28.0; 19F NMR (376 MHz, CDCl3) δ −83.0, −124.3;
HRMS (ESI) m/z calcd for C13H11F5O3 310.0628, found 310.0634.
Perfluoroheptan(2-phenylethyl)one (3r): colorless oil; yield 98%
(2.47 g); 1H NMR (400 MHz, CDCl3) δ 7.19−7.33 (m, 5H), 3.08 (t, J
= 8.0 Hz, 2H), 2.99 (t, J = 8.0 Hz, 2H); 13C NMR (100 MHz, CDCl3)
δ 193.0 (q, J = 26.0 Hz), 139.4, 128.4, 128.2, 126.8, 106.7−118.8 (m),
39.8, 28.6; 19F NMR (376 MHz, CDCl3) δ −81.9, −121.1−−127.1
(m); HRMS (ESI) m/z calcd for C16H9F15O 502.0414, found
502.0418.
ASSOCIATED CONTENT
■
S
* Supporting Information
NMR spectra for 3a−r, 5r, and 5s. This material is available
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
(34) Trabelsi, H.; Cambon, A. Synthesis 1992, 315−319.
(35) Jukic, M.; Sterk, D.; Casar, Z. Curr. Org. Synth. 2012, 9, 488−
512.
ACKNOWLEDGMENTS
■
We gratefully acknowledge the financial support of the
Fundamental Research Funds for the Central Universities
(No. DUT13LAB03) and SRF for ROCS, SEM. We also thank
Prof. Baomin Wang, Dr. Yuming Song, and Dr. Ying Peng for
valuable discussions.
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Int. Ed. 2007, 46, 7793−7795.
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