Full Papers
employing nitrobenzene as an internal standard or by column
chromatography.
Keywords: acidity · alcohols · electron transfer · oxidation
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1
7
-(4-Bromophenyl)ethanone: H NMR (400 MHz, CDCl ): d=7.85–
3
[1] G. Tojo, M. Fernµndez, Oxidation of Alcohols to Aldehydes and Ketones,
Springer, New York, 2010.
13
.80 (m, 2H), 7.63–7.59 (m, 2H), 2.59 ppm (s, 3H). C NMR
(
101 MHz, CDCl ): d=197.0, 135.8, 131.9, 129.8, 128.3, 26.6 ppm.
3
1
1
-(4-Chlorophenyl)propan-1-ol: H NMR (400 MHz, CDCl ): d=7.93–
3
7
.88 (m, 2H), 7.46–7.41 (m, 2H), 2.98 (q, J=7.2 Hz, 2H), 1.22 ppm
[
1
3
(
t, J=7.2 Hz, 3H). C NMR (101 MHz, CDCl ): d=199.5, 139.4, 135.2,
3
1
29.4, 128.9, 31.8, 8.2 ppm.
[
1
2
7
7
,3-Dihydro-1H-inden-1-one: H NMR (400 MHz, CDCl ): d=7.80–
3
.73 (m, 1H), 7.59 (td, J=7.6, 1.2 Hz, 1H), 7.53–7.45 (m, 1H), 7.42–
.33 (m, 1H), 3.20–3.11 (m, 2H), 2.74–2.66 ppm (m, 2H). C NMR
[5] a) M. V. N. De Souza, Mini-Rev. Org. Chem. 2006, 3, 155; b) F. Minisci, F.
13
(
101 MHz, CDCl ): d=207.1, 155.2, 137.1, 134.6, 127.3, 126.7, 123.7,
3
002, 35, 774; d) R. A. Sheldon, I. W. C. E. Arends, J. Mol. Catal. A 2006,
7
7.4, 77.1, 76.7, 36.2, 25.8 ppm.
2
51, 200; e) P. L. Bragd, H. Van Bekkum, A. C. Besemer, Top. Catal. 2004,
1
3
8
2
,4-Dihydronaphthalen-1(2H)-one: H NMR (400 MHz, CDCl ): d=
.06–8.00 (m, 1H), 7.47 (td, J=7.5, 1.4 Hz, 1H), 7.34–7.23 (m, 2H),
.97 (t, J=6.1 Hz, 2H), 2.70–2.62 (m, 2H), 2.17–2.11 ppm (m, 2H).
27, 49.
3
2559; b) P. L. Anelli, S. Banfi, F. Montanari, S. Quici, J. Org. Chem. 1989,
54, 2970; c) T. Inokuchi, S. Matsumoto, T. Nishiyama, S. Torii, J. Org.
1
3
C NMR (101 MHz, CDCl ): d=198.4, 144.5, 133.4, 132.6, 128.8,
3
1
27.2, 126.6, 39.2, 29.7, 23.3 ppm.
1
6
,7,8,9-Tetrahydro-5H-benzo[7]annulen-5-one: H NMR (400 MHz,
CDCl ): d=7.71 (dd, J=7.7, 1.3 Hz, 1H), 7.40 (td, J=7.5, 1.4 Hz,
3
1
2
H), 7.27 (d, J=7.5 Hz, 1H), 7.18 (d, J=7.5 Hz, 1H), 2.96–2.87 (m,
H), 2.77–2.67 (m, 2H), 1.91–1.74 ppm (m, 4H). C NMR (101 MHz,
1
3
CDCl ): d=206.2, 141.3, 138.8, 132.2, 129.7, 128.5, 126.6, 40.8, 32.5,
3
2
5.2, 20.9 ppm.
1
Benzophenone: H NMR (400 MHz, CDCl ): d=7.88–7.77 (m, 4H),
3
[
Liu, S. H. Li, B. Chen, J. J. Cheng, J. Q. Kuang, Y. Liu, B. Q. Wan, Y. L.
7
4
1
.59 (ddd, J=8.4, 2.3, 1.1 Hz, 2H), 7.48 ppm (dd, J=10.4, 4.6 Hz,
H). C NMR (100 MHz, CDCl3): d=196.8, 137.6, 132.4, 130.1,
28.3 ppm.
1
3
1
(
4-Chlorophenyl)(phenyl)methanone: H NMR (400 MHz, CDCl ): d=
3
[
7
.84–7.71 (m, 4H), 7.65–7.56 (m, 1H), 7.55–7.41 ppm (m, 4H).
1
3
C NMR (100 MHz, CDCl ): d=195.5, 138.9, 137.3, 135.9, 132.7,
3
[
1
31.5, 129.9, 128.7, 128.4 ppm.
1
(
2-Chlorophenyl)(phenyl)methanone: H NMR (400 MHz, CDCl ): d=
3
7
7
1
.82 (dt, J=8.5, 1.5 Hz, 2H), 7.65–7.55 (m, 1H), 7.53–7.41 (m, 4H),
13
.41–7.32 ppm (m, 2H). C NMR (100 MHz, CDCl ): d=195.3, 138.6,
3
36.5, 133.7, 131.3, 131.1, 130.1, 129.1, 128.6, 126.7 ppm.
1
Phenyl(p-tolyl)methanone: H NMR (400 MHz, CDCl ): d=7.79 (dt,
3
[
[
J=8.4, 1.6 Hz, 2H), 7.75–7.70 (m, 2H), 7.61–7.54 (m, 1H), 7.52–7.44
13
(
m, 2H), 2.44 ppm (s, 3H). C NMR (101 MHz, CDCl ): d=196.5,
3
1
43.2, 138.0, 134.9, 132.2, 130.3, 129.9, 129.0, 128.2, 21.7 ppm.
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1
-(Pyridin-2-yl)ethanone: H NMR (400 MHz, CDCl ): d=8.70 (ddd,
3
J=4.7, 1.6, 0.8 Hz, 1H), 8.05 (dt, J=7.9, 1.0 Hz, 1H), 7.84 (td, J=7.7,
1
.7 Hz, 1H), 7.48 (ddd, J=7.6, 4.8, 1.2 Hz, 1H), 2.74 ppm (s, 3H).
[
1
3
C NMR (101 MHz, CDCl ): d=200.1, 153.5, 148.9, 136.9, 127.1,
3
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21.7, 25.8 ppm.
[
[
1
Methyl 2-oxo-2-phenylacetate: H NMR (400 MHz, CDCl ): d=8.06–
3
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.98 (m, 2H), 7.71–7.63 (m, 1H), 7.57–7.48 (m, 2H), 4.02–3.94 ppm
m, 3H). C NMR (101 MHz, CDCl ): d=186.1, 164.0, 135.0, 132.4,
3
1
3
(
1
30.1, 128.9, 52.8 ppm.
Acknowledgements
We are grateful to the National Natural Science Foundation of
China (NO. 21103207 and 21133011) and the western light pro-
gram of the Chinese Academy of Sciences (2012).
53, 3014; h) S. J. Yu, C. X. Miao, D. Q. Wang, S. F. Wang, C. G. Xia, W.
Sun, J. Mol. Catal. A 2012, 353, 185.
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