2232
L. Yu et al. / Journal of Organometallic Chemistry 696 (2011) 2228e2233
321 (22) [Mþ ꢂ PhSe], 183 (100), 128 (95); HRMS (ESI): m/z calcd for
C22H19ClNaSe2 (M þ Na)þ 500.9403, Found 500.9415.
4.3.4. Compound 3d
4.3.11. Compound 2a
Oil IR (film): 2941, 1575, 1475, 1436, 1301, 1022, 784, 738,
Oil. IR (film): 1638, 1479, 1436, 1385, 1134, 1070, 1015, 913, 740,
692 cmꢂ1
;
1H NMR (600 MHz, CDCl3, TMS):
d
7.30e7.40 (m, 14H),
3.84e3.85 (m, 1H), 2.63e2.64 (m, 1H), 2.25e2.27 (m, 1H), 2.09e2.11
(m, 1H), 1.94e1.96 (m, 1H); 13C NMR (150 MHz, CDCl3):
22.3, 31.7,
691. 1H NMR (600 MHz, CDCl3, TMS):
d
7.15e7.34 (m, 14H), 4.55 (s,
1H), 1.13e1.39 (m, 4H). 13C NMR (150 MHz, CDCl3): (E and Z
mixture) 14.5,15.6, 27.1, 56.3,121.0,127.3,127.4,128.7,128.9,129.0,
d
d
49.2, 55.5, 125.2, 127.2, 127.6, 128.5, 128.8, 129.0, 129.1, 129.2, 129.3,
130.1, 130.3, 131.3, 133.3, 133.5, 140.8. MS (EI, 70 eV): m/z (%) 522 (2)
[Mþ], 365 (29) [Mþ ꢂ PhSe], 128 (100). HRMS (ESI): m/z calcd for
C22H19BrNaSe2 (M þ Na)þ 544.8898, Found 544.8885.
1
133.2, 134.0, 136.8, 138.0, 141.8; MS (EI, 70 eV): m/z (%) 478 (1)
[Mþ], 340 (70) [Mþ ꢂ p-ClC6H4CHCH2], 321 (24) [Mþ ꢂ PhSe], 183
(100); HRMS (ESI): m/z calcd for C22H19ClNaSe2 (M þ Na)þ
500.9403, Found 500.9423.
4.3.12. Compound 4j
Oil. IR (film): 3069, 2926, 2851, 1578, 1476, 1438, 1384, 1022, 998,
4.3.5. Compound 3e
734, 690, 669 cmꢂ1 1H NMR (600 MHz, CDCl3, TMS):
d 7.20e7.42 (m,
Oil. IR (film): 3054, 2982, 2942, 1514, 1475, 1436, 1021, 913, 816,
10H), 3.03 (t, J ¼ 7.8 Hz, 2H), 2.74 (t, J ¼ 7.8 Hz, 2H), 2.56 (t, J ¼ 5.7 Hz,
742, 693 cmꢂ1 1H NMR (600 MHz, CDCl3, TMS):
; d 7.16e7.72 (m,
2H), 2.27 (t, J ¼ 5.7 Hz, 2H), 1.56e1.57 (m, 6H). 13C NMR (150 MHz,
14H), 3.81e3.84 (m, 1H), 2.63e2.66 (m, 1H), 2.35 (s, 3H), 2.20e2.25
CDCl3): d 26.6, 26.7, 28.3, 28.4, 31.3, 35.8, 36.2, 121.8, 126.2, 126.5,
(m, 1H), 2.06e2.09 (m, 1H), 1.89e1.93 (m, 1H); 13C NMR (150 MHz,
129.0,129.1,130.5,131.0,132.0,132.1,148.9. MS(EI, 70eV): m/z(%)436
CDCl3): d 21.3, 22.4, 31.8, 49.3, 56.5, 126.9, 127.8, 128.3, 128.5, 128.7,
(11) [Mþ], 279 (45) [Mþ ꢂ PhSe], 79 (100). (Known compound) [8].
128.8, 129.1, 129.2, 130.5, 131.6, 136.7, 138.1; MS (EI, 70 eV): m/z (%)
458 (1) [Mþ], 340 (25), 183 (100), 128 (60); Anal. Calcd for
C23H22Se2: C, 60.54; H, 4.86. Found: C, 60.23; H, 4.71.
4.3.13. Compound 4k
Oil. IR (film): 3058, 2924, 2853,1631,1579,1476,1437,1384,1119,
1068, 1022, 1000, 735, 693, 668 cmꢂ1 1H NMR (600 MHz, CDCl3,
4.3.6. Compound 3f
TMS):
2H), 2.72e2.82 (m, 4H), 1.99e2.12 (m, 4H), 1.51e1.55 (m, 2H). 13C
NMR (150 MHz, CDCl3): 26.8, 30.9, 35.3, 35.5, 35.8, 35.9, 44.4,
d
7.20e7.44 (m, 15H), 3.36e3.38 (m, 1H), 3.06 (t, J ¼ 7.2 Hz,
Oil. IR (film): 3055, 2962, 2904, 2866, 1475, 1436, 1021, 913, 831,
742, 693 cmꢂ1
;
1H NMR (600 MHz, CDCl3, TMS):
d
7.27e7.73 (m,
d
14H), 3.81e3.84 (m, 1H), 2.64e2.68 (m, 1H), 2.21e2.26 (m, 1H),
122.8, 126.2, 126.3, 126.6, 126.8, 128.4, 129.0, 129.1, 130.4, 131.3,
131.8, 132.2, 146.3, 147.2. MS (EI, 70 eV): m/z (%) 512 (7) [Mþ], 355
(27) [Mþ ꢂ PhSe], 91 (100). (Known compound) [8].
2.06e2.09 (m, 1H), 1.89e1.94 (m, 1H), 1.34 (s, 9H); 13C NMR
(150 MHz, CDCl3):
d 22.4, 31.5, 31.8, 34.6, 49.3, 56.5, 125.0, 126.8,
128.3, 128.4, 128.7, 129.1, 129.2, 130.5, 136.6, 136.8, 138.1, 149.9; MS
(EI, 70 eV): m/z (%) 500 (1) [Mþ], 340 (12), 183 (100); Anal. Calcd for
C26H28Se2: C, 62.65; H, 5.66. Found: C, 62.28; H, 5.43.
4.3.14. Compound 4l
Solid. m.p. 78e80 ꢀC; 1H NMR (600 MHz, CDCl3, TMS):
d
7.06e7.45 (m, 20H), 3.02 (t, J ¼ 7.2 Hz, 2H), 2.71 (t, J ¼ 7.5 Hz, 2H);
4.3.7. Compound 3g
13C NMR (150 MHz, CDCl3):
d
26.8, 35.3, 126.3, 127.2, 127.4(d), 128.0,
Oil. IR (film): 2925, 2862, 1578, 1476, 1436, 1022, 910, 739,
128.3, 128.4, 128.9, 129.1 (d), 129.2, 130.3, 131.6, 132.9, 133.7, 141.5,
143.3, 147.1. (Known compound) [7,8].
692 cmꢂ1 1H NMR (600 MHz, CDCl3, TMS):
; d 7.31e7.76 (m, 10H),
2.51e2.57 (m, 1H), 2.08e2.18 (m, 2H), 1.86e1.93 (m, 1H), 1.73e1.78
(m, 1H), 1.62e1.66 (m, 1H), 1.45e1.49 (m, 1H), 1.20e1.32 (m, 10H),
4.3.15. Compound 5
0.90 (t, J ¼ 7.2 Hz, 3H); 13C NMR (150 MHz, CDCl3):
d
14.2, 22.7, 24.9,
Solid. m.p. 105e107 ꢀC; 1H NMR (600 MHz, CDCl3, TMS):
27.0, 29.2, 29.6, 31.9, 32.1, 33.5, 48.7, 56.3, 128.3, 128.5, 128.7 (d),
128.8, 130.3, 136.6, 137.8; MS (EI, 70 eV): m/z (%) 465 (1) [Mþ ꢂ 1],
309 (100) [Mþ ꢂ PhSe]; Anal. Calcd for C23H30Se2: C, 59.48; H, 6.51.
Found: C, 59.26; H, 6.20.
d
7.21e7.50 (m,15H), 3.61 (t, J ¼ 6.6 Hz, 2H), 2.73 (t, J ¼ 6.6 Hz, 2H); 13
C
NMR (150MHz, CDCl3):d 36.9, 43.7,127.3,127.6 (d),128.1,128.4,129.0,
129.3,129.5,130.0,133.7,141.4,143.2,148.9. (Known compound) [31].
Acknowledgment
4.3.8. Compound 3h
Oil. IR (film): 2924, 2854, 1576, 1467, 1443, 1236, 1012, 734,
This work was supported by the Natural Scientific Foundation of
Jiangsu Province (NO. BK2010321), University Natural Scientific
Foundation of Jiangsu Province (NO. 09KJB150014), the 45th Post-
doctor foundation of China (NO. 20090451249) and the National
Natural Scientific Foundation of China (NO. 20633010 and
20773106). We thank Prof. Chaoguo Yan, Miss Liting Du and Miss
Limin Yuan for the assistances in X-ray diffraction analysis.
686 cmꢂ1 1H NMR (600 MHz, CDCl3, TMS):
; d 7.30e7.75 (m, 10H),
2.53e2.55 (m, 1H), 2.08e2.16 (m, 2H), 1.88e1.91 (m, 1H), 1.74e1.77
(m, 1H), 1.63e1.65 (m, 1H), 1.45e1.49 (m, 1H), 1.22e1.32 (m, 14H),
0.89 (t, J ¼ 6.6 Hz, 3H); 13C NMR (150 MHz, CDCl3):
d 13.3, 21.8, 24.0,
26.1, 28.5, 28.6, 28.7, 31.0, 31.2, 32.6, 47.8, 55.4,127.4,127.6,127.8 (d),
127.9, 129.4, 135.7, 136.8; MS (EI, 70 eV): m/z (%) 493 (1) [Mþ ꢂ 1],
337 (100) [Mþ ꢂ PhSe]; Anal. Calcd for C25H34Se2: C, 60.97; H, 6.96.
Found: C, 60.65; H, 6.61.
Appendix A. Supplementary materials
4.3.9. Compound 3i
CCDC 780201 contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
(Trace, only observed from 1H NMR of p-Chloro acetophenone).
1H NMR (600 MHz, CDCl3, TMS):
(m, 1H), 3.02e3.06 (m, 1H), 2.46e2.48 (m, 1H), 2.15e2.18 (m, 1H),
d 7.27e7.90 (m, 14H), 3.18e3.23
1.93 (s, 1H), 1.53 (s, 3H).
Appendix A. Supporting information
4.3.10. p-Chloro acetophenone
1H NMR (600 MHz, CDCl3, TMS):
3H). Known compound and the spectrums were accordance to
d
7.44e7.91 (m, 4H), 2.60 (s,
Supplementary data related to this article can be found online at