Paper
RSC Advances
for the synthesized compound 1: C, 42.17%; H, 4.6%; N, 7.20%. General procedure for the oxidation of thianthrene 5-oxide
Found: C, 42.55%; H, 4.5%; N, 6.98%. UV-Vis [lmax; nm
ꢁ3
Catalyst (2.5 ꢂ 10 mmol), thianthrene 5-oxide (1 mmol), H O2
2
ꢁ
1
ꢁ1
(
(
3; L cm mol ) in methanol; Fig. S5, ESI†]: 230 (57 420), 263
35 100). IR (KBr pellet, cm ; Fig. S6, ESI†): 3336(s), 2928(m),
(
1 mmol) and methanol (5 mL) were added to a glass tube; then
ꢁ
1
ꢀ
the catalytic reaction was performed at 25 C for 15 min. Aer
the reaction was completed, the resulting mixture was analyzed
by HPLC-MS and HPLC.
1
1
6
654(w), 1626(w), 1582(w), 1519(m), 1424(s), 1222(w), 1136(w),
118(w), 1104(s), 1065(s), 921(m), 870(m), 845(s), 735(m), 724(s),
46(m), 602(m), 429(m). H NMR [DMSO-d6, 25 C, 400 MHz;
1
ꢀ
d (ppm)] (Fig. S7, ESI†): 9.25 (d, J ¼ 6.3 Hz, 2H), 8.89 (d, J ¼
8
.2 Hz, 2H), 8.25 (s, 2H), 8.08 (dd, J ¼ 8.2, 4.7 Hz, 2H), 3.44 (q, J Conflicts of interest
1
3
¼
7.0 Hz, 4H), 1.05 (t, J ¼ 7.0 Hz, 6H). C NMR [DMSO-d6,
There are no conicts to declare.
ꢀ
2
5
C, 126 MHz, d (ppm)] (Fig. S8, ESI†): 148.25, 140.54,
139.45, 129.32, 127.34, 125.13, 55.96, 18.44.
Thianthrene 5-oxide: a soln of MCPBA (878 mg, 5.08 mmol)
Acknowledgements
in CH
2
Cl
2
(15 mL) was added to a stirred solution of thianthrene
Cl (15 mL) cooled in an ice bath under
. Aer 1 h, the mixture was extracted with sat. aq. NaHCO
O (2 ꢂ
5 mL), then dried (MgSO ) and concentrated under vacuum.
This work was nancially supported by the Zhejiang Provincial
Natural Science Foundation of China (LQ16B030004) and the
Natural Science Foundation (Y201224604) for the Education
Ministry of Zhejiang Province.
(
N
(
2
1.0 g, 4.62 mmol) in CH
2
2
2
3
3 ꢂ 15 mL). The organic layer was washed with H
2
4
The sample was then chromatographed on silica gel utilizing
petroleum ether/ethyl acetate (6 : 1) as eluent to give thian-
Notes and references
1
ꢀ
threne oxide in a good yield. H NMR [CDCl
MHz; d (ppm)]: 7.93 (d, J ¼ 7.8 Hz, 2H), 7.63 (d, J ¼ 7.7 Hz, 2H),
.56 (t, J ¼ 7.6 Hz, 2H), 7.43 (t, J ¼ 7.5 Hz, 2H).
3
-d6, 25 C, 500
1 (a) J. Li, L. Wang, Y. Q. Ye, X. Fu, Q. Ren, H. Zhang and
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7
X-ray crystallographic determination
(
d) R. Afrasiabi, F. Jalilian, B. Yadollahi and M. R. Farsani,
Diffraction data of the titanium complex were collected at 293 K
for compound 1 on an Oxford Diffraction Xcalibur CCD
diffractometer using graphite monochromated Mo-Ka radiation
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˚
(
l ¼ 0.71073 A). Absorption correction was applied using mul-
tiscan technique. The structure was solved by direct method
and rened by full-matrix least-squares method using the
19
program SHELXL-97 within WINGX. All non-hydrogen atoms
were easily found from the Fourier difference maps and rened
with anisotropic temperature parameters. The graphics was
drawn by the ORTEP. The detailed crystallographic data and
structure renement parameters for the compound were
recorded in Table S2.† Selected bond distances and angles for
them are listed in Table S3 (see the ESI†).
1
0, 447; (i) J. M. Shin, Y. M. Cho and G. Sachs, J. Am.
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(
b) S. O. Ribeiro, D. Juli ˜a o, L. Cunha-Silva,
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In a typical experiment, suldes (1.00 mmol) and catalyst (2.5 ꢂ
ꢁ3
10
mmol) in methanol (5 mL) was stirred at 298 K tempera-
ture for 10 min and then 30% hydrogen peroxide (1.00 mmol)
was introduced as the oxidant. At the end of specied time,
aliquots of 100 mL reaction mixture were taken at regular
intervals, treated with in 300 mL of methanol and then analyzed
by GC/MS and GC.
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6 4 3
General procedure for oxidation of p-ClC H SCH and
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C H SOCH
3
6
5
ꢁ
3
Catalyst (2.5
ꢂ
10
mmol), p-ClC
6
H
4
SCH
3
(1 mmol),
C
6
H
5
SOCH (1 mmol), H
3
2
O
2
(1 mmol) and methanol (5 mL)
were added to a glass tube; then the catalytic reaction was
ꢀ
performed at 25 C for 15 min. Aer the reaction was
completed, the resulting mixture was analyzed by GC-MS
and GC.
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RSC Adv., 2017, 7, 44259–44264 | 44263