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addition of water (1 mL) and stirred for 30 min. All volatiles
were removed under vacuum; the residue was extracted with
dichloromethane and ltered through a pad of Celite. The
ltrate was concentrated to dryness and the crude product was
puried by column chromatography (SiO2, hexane/ethyl acetate:
5/1) to yield 9a as a colourless solid. Single crystals suitable for
X-ray diffraction were grown by slow evaporation of an ethyl
acetate/hexane (1/1) mixture of compound 9a at room temper-
ature. Yield: 0.20 g (81%). Mp: 172–176 ꢁC (decomp.). Anal.
calcd for C22H28N2O2S: C, 68.72; H, 7.34; N, 7.29. Found: C,
68.97; H, 7.48; N, 7.48. 1H NMR (CDCl3, 500 MHz): d 2.26
(m, 18H, CH3Mes), 3.31 (s, 3H, OCH3), 4.94 (d, J ¼ 1 Hz, 1H,
CHim-4-OMe), 5.32 (d, 1H, J ¼ 1 Hz, CHim-5-OH), 6.94 (m, 4H,
CHMes). 13C NMR (CDCl3, 125 MHz): d 17.7 (CH3Mes), 18.6
(CH3Mes), 18.9 (CH3Mes), 21.2 (CH3Mes), 57.6 (OCH3), 88.9, 98.4,
129.6, 132.1, 133.3, 135.8, 136.5, 138.5, 138.8, 139.3, 181.3
(C]S). IR (KBr, cmꢀ1): 3319 (m), 2921 (m), 2856 (w), 1645 (w),
1609 (w), 1484 (vs), 1450 (s), 1393 (m), 1377 (m), 1323 (vs), 1242
(s), 1193 (w), 1075 (s), 972 (w), 850 (w), 739 (w), 682 (w), 581 (w)
cmꢀ1. ESI-MS: calcd 385.1944, found 385.1952 (M + H+)+.
Synthesis of compound 9b. Compound 9b was prepared
using a procedure similar to that for compound 9a. Compound
8 (0.817 g, 1.86 mmol), KHMDS (9 mL, 4.5 mmol), selenium
(0.220 g, 2.79 mmol) and dry THF (80 mL) were used. Aer
evaporation of all volatiles, the crude product was puried by
column chromatography (SiO2, hexane/ethyl acetate: 5/1) to
yield 9b as a pale yellow coloured solid. Yield: 0.54 g (67%). Mp:
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ꢁ
156–158 C (decomp.). Anal. calcd for C22H28N2O2Se: C, 61.25;
H, 6.54; N, 6.49. Found: C, 62.78; H, 6.86; N, 6.58. 1H NMR
(CDCl3, 500 MHz): d 2.21 (m, 18H, CH3Mes), 3.30 (s, 3H, OCH3),
4.91 (d, J ¼ 1.5 Hz, 1H, CHim-4-OMe), 5.29 (d, J ¼ 1.5 Hz, 1H,
CHim-5-OH), 6.93 (m, 4H, CHMes). 13C NMR (CDCl3, 125 MHz):
d 17.7 (CH3Mes), 18.7 (CH3Mes), 19.0 (CH3Mes), 21.3 (CH3Mes), 57.9
(OCH3), 89.8, 99.4, 129.6, 132.7, 133.9, 135.6, 136.3, 138.7, 138.9,
139.1, 182.2 (C]Se). 77Se NMR (CDCl3, 76 MHz): d 167.3 (C]
Se). IR (KBr, cmꢀ1): 3285 (w), 2922 (s), 2854 (w), 1644 (w), 1609
(w), 1483 (vs), 1456 (vs), 1376 (m), 1312 (vs), 1292 (vs), 1239 (s),
1192 (w), 1073 (vs), 850 (w), 733 (w), 655 (w), 577 (w) cmꢀ1. ESI-
MS: calcd 433.1389, found 433.1397 (M + H+)+.
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Acknowledgements
This study was supported by the Department of Science and
Technology (DST) and the Council of Scientic and Industrial
Research (CSIR), the Government of India. V. G. (UGC and DST)
and V. K. (CSIR) thank funding agencies and institute for their
doctoral fellowships. Moreover, the authors thank the institute
for their infrastructure.
¨
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Notes and references
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RSC Adv., 2015, 5, 87888–87896 | 87895