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475.8. Anal. calcd. for C13H12Se: C, 62.90; H, 4.83, Se,
32.25. Found C, 62.28; H, 4.75; Se, 32.66%.
2-cyclohexenyl-1-naphthyl selenide, [1-C10H7SeC6H9]
59.72; H, 4.07, Se, 32.25. Found C, 59.24; H, 4.05; Se,
32.51%.
1,3-Bis(1-naphthylseleno)propane, [1-C10H7Se(CH2)3-
Se(1-C10H7)] (12). Colorless crystalline solid; m.p. 73–
1
(7). Yellow oil; H NMR: d 8.35–8.38 (d, 1H, 8.4 Hz),
1
7.56–7.71 (m, 3H), 7.27–7.38 (m, 2H), 7.15–7.20 (m, 1H),
5.72–5.77 (m, 1H), 5.57–5.61 (m, 1H), 3.80(d, 1H, 1.8 Hz),
1.85–1.96 (m, 4H), 1.71–1.77(m, 2H); 13C NMR: d 134.90,
134.00,133.76,130.24, 129.60, 128.63, 128.50, 128.16,
127.72, 126.53, 126.05, 125.66, 41.36, 29.27, 24.94, 19.58;
IR (KBr, m cmꢀ1): 3051.4, 3024.9, 2926.9, 2856.3, 2831.7,
1587.9, 1560.2, 1534.0, 1500.3, 1438.5, 1021.1, 770.3,
732.5, 588.2, 534.3, 453.7. Anal. calcd. for C16H18Se: C,
66.6; H, 5.55, Se, 27.7. Found C, 66.0; H, 5.2; Se, 26.9%.
Allyl-1-naphthyl telluride, [1-C10H7TeCH2CH@CH2]
(8). Yellow viscous oil, 1H NMR: d 8.09–8.12 (d, 1H,
8.7 Hz), 7.86–7.88 (dd, 1H, 6.9, 1.2 Hz), 7.50–7.58 (m,
2H), 7.25–7.34 (m, 2H), 7.05–7.13 (m, 1H), 5.72–5.87 (m,
1H), 4.45–4.46 (m, 2H), 3.34–3.41 (d, 2H, 9 Hz); 13C
NMR: d 139.7, 136.5, 135.8, 133.5, 132.7, 129.4, 128.7,
75 ꢁC; H NMR: d 8.31–8.33 (d, 1H, 7.5 Hz), 7.76–7.79
(d, 1H, 7.5 Hz), 7.69–7.72 (d, 1H, 8.1 Hz), 7.61–7.63 (d,
1H, 7.5 Hz), 7.15–7.20 (t, 1H), 7.42–7.52 (doublet of quin-
tet, 2H), 7.21–7.26 (t, 1H, 7.8 Hz), 2.93–2.98 (t, 2H,
6.9 Hz), 1.87–1.97 (m, 1H, 7.2, 3.9 Hz); 13C NMR: d
134.28, 133.95, 132.35, 129.08, 128.64, 128.30, 127.2,
126.64, 126.20, 125.73, 30.15, 27.69; 77Se NMR: d 227.4;
IR (KBr, m cmꢀ1): 3042.0, 2918.5, 2854 560.1, 1508.1,
1448.4, 1438.1, 1420.1, 1021.0, 961.9, 541.0, 532.1, 420.5;
UV/vis (kmax nm, CH3CN): 308, 284, 245. Anal. calcd.
for C23H20Se2: C, 60.52; H, 4.38, Se, 35.08. Found C,
59.93; H, 4.04; Se, 35.02%.
3.3.4. Symmetrical 1,10-dinaphthyl diselenides/ditellurides
Bis(1-naphthyl) diselenide, [1-C10H7Se]2 (13). Yellow
126.7, 126.1, 126.0, 116.4, 115.3, 25.0; IR (KBr, m cmꢀ1
)
crystalline solid; m.p. 85–87 ꢁC; H NMR: d 7.90–7.98 (d,
1
3049.9, 2955.0, 2925.5, 2869.0, 1585.9, 1556.0, 1499.6,
1454.1, 1376.3, 1330.0, 1041.1, 1020.8, 769.0, 672.7,
522.7, 403.9. Anal. calcd. for C, 53.24; H, 4.09. Found C,
53.07; H, 3.92%.
2H, 8.1 Hz), 7.45–7.50 (t, 6H, 7.5 Hz), 7.08–7.22 (m, 4H),
6.91–6.96 (t, 2H); 13C NMR: d 134.13, 130.27, 129.78,
128.54, 128.22, 127.99, 126.62, 126.26, 125.81, 125.57;
77Se NMR: d 429.7; IR (KBr, m cmꢀ1): 3053.8, 2925.8,
2854.2, 1588.3, 1560.2,1504.0, 1384.1, 1334.6, 1198.0,
782.4, 650.1, 530.5, 409.0; UV/vis (kmax nm, CH3CN):
300. Anal. calcd. for C20H14Se2: C, 59.45; H, 4.50, Se,
36.03. Found C, 59.20; H, 4.25; Se, 35.98%.
Benzyl-1-naphthyl telluride, [1-C10H7TeCH2C6H5] (9).
1
Pale yellow waxy solid; H NMR: d 8.10–8.19 (m, 1H),
7.89–7.91 (d, 1H, 6.9 Hz), 7.62–7.71 (m, 2H), 7.34–7.43
(m, 2H), 7.10–7.15 (m, 1H), 6.90–7.05(m, 5H), 4.11(s,
2H); 13C NMR: d 140.27, 136.56, 133.49, 132.92, 129.67,
128.88, 128.77, 128.39, 128.25, 126.81, 126.16, 126.12,
126.07, 117.06, 12.07; IR (KBr, m cmꢀ1): 3050.3, 2924.6,
2852.2, 1598.1, 1555.3, 1492.1, 1383.3, 1329.9, 1056.8,
1020.4, 951.2, 769.0, 694.7, 521.5, 441.7. Anal. calcd. for
C, 60.17; H, 4.12. Found C, 59.67; H, 4.02%.
Bis (1-naphthyl)ditelluride, [1-C10H7Te]2 (14). Red
1
crystalline solid; m.p. 119–120 ꢁC; H NMR: d 8.13–8.15
(d, 2H, 7.2 Hz), 8.00–8.03 (d, 2H, 8.4 Hz), 7.75–7.80 (dd,
4H, 14.4, 8.4 Hz), 7.43–7.47 (m, 2H), 7.30–7.34(t, 2H,
7.2 Hz), 7.19–7.23 (t, 2H, 7.6 Hz); 13C NMR: d 140.8,
136.4, 133.6, 133.1, 130.2, 128.7, 126.7, 126.2, 126.1,
111.5; 77Se NMR: d 429.7; IR (KBr, m cmꢀ1): 3054.2,
2926.7, 2854.7, 1584.4, 1562.6, 1548.1, 1493.2, 1467.8,
1426.0, 1008.1, 793.5, 530.1, 522.4, 464.1, 428.3; 125Te
NMR: d 357.0; UV/vis (kmax nm, CH3CN): 291, 289. Anal.
calcd. for C20H14Te2: C,47.61; H, 2.77. Found C, 47.22, H,
2.32%.
3.3.3. a,x-Bis(1-naphthylseleno)alkanes
Bis(1-naphthylseleno) methane, [(1-C10H7Se)2CH2]
(10). Colourless viscous oil; 1H NMR: d 8.12–8.06 (d,
2H), 7.63–7.56 (m, 6H), 7.31–7.25 (m, 4H), 7.10–7.13 (t,
2H), 4.06 (s, 2H); 13C NMR: d 134.24, 134.05, 133.20,
130.11, 128.98, 128.61, 127.66, 126.70, 126.15, 125.65,
21.36; 77Se NMR: d 285.08; IR (KBr, m cmꢀ1): 3051.3,
2924.6, 2853.0, 1561.0, 1501.3, 1454.1, 1377.4, 1333.7,
1021.3, 960.3, 769.0, 735.8, 621.6, 530.2, 410.4; UV/vis
(kmax nm, CH3CN): 310, 286. Anal. calcd. for C21H16Se2:
C, 58.87; H, 3.73, Se, 37.38. Found: C, 59.01; H, 3.65;
Se, 37.18%.
1,2-Bis(1-naphthylseleno)ethane, [1-C10H7Se(CH2)2Se-
(1-C10H71)] (11). Colourless crystalline solid; m.p. 112–
114 ꢁC; 1H NMR: d 8.23–8.26 (m, 2H), 7.67–7.77 (m,
4H), 7.50–7.53 (d, 2H, 7.2 Hz), 7.38–7.47 (m, 4H), 7.13–
7.16 (m, 2H), 3.07 (s, 4H); 13C NMR: d 134.65,134.16,
132.73, 129.15, 128.65, 128.56, 127.82, 126.72, 126.24,
125.65, 27.44; 77Se NMR: d 276.02; IR (KBr, m cmꢀ1):
2925.0, 2853.9, 1585.5, 1548.1, 1498.7, 1467.5, 1415.6,
1020.3, 651.4, 573.4, 531.9, 408.3; UV/vis (kmax nm,
CH3CN): 306, 285 nm. Anal. calcd. for C22H18Se2: C,
4. Supplementary material
Crystallographic information (excluding structure fac-
tors) has been deposited in the crystallographic information
file (CIF) format with the Cambridge Crystallographic
Data Center as supplementary Publication No. CCDC
Nos. 221480 and 246467 for compound 2 and 3, respec-
tively. Copies of this information may be obtained free of
charge from the Director, CCDC, 12-Union Road, Cam-
bridge CB21E2, UK (fax: +44 1223 336033; e-mail:
deposit@ccdc.cam.ac.uk).
Acknowledgments
The financial assistance from DST, New Delhi, vide
Sanction No. SR/SI/IC-02/2003 is gratefully acknowledged.