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A. Bhalla et al. / Journal of Organometallic Chemistry 694 (2009) 179–189
3.3.5. Ethyl 2-(5-methyl)pyridylselenopropanoate [(5-CH3C5H3N)Se
(CH2)2COOC2H5] (9b)
128.66, 128.47, 127.74, 126.78, 126.27, 125.75, 60.67, 35.36,
21.96, 14.19; 77Se NMR: d 253.87; IR (CHCl3, cmÀ1): 1735.8.
m
Yield 92%; yellow oil; 1H NMR: d 8.03 (s, 1H), 7.01–7.12 (m, 2H),
3.97–4.03 (q, 2H, 7.2 Hz), 3.55–3.61 (t, 2H, 7.1 Hz), 2.54–2.58 (t,
2H, 7.1 Hz), 2.19 (s, 3H), 1.02–1.07 (t, 3H, 7.2 Hz); 13C NMR: d
171.27, 150.03, 149.67, 136.34, 129.74, 124.43, 60.59, 34.83,
3.3.12. Ethyl 2-naphthylselenobutanoate [(1-C10H7)Se(CH2)3COOC2H5]
(11c)
Yield 86%; greenish-yellow oil; 1H NMR: d 8.36–8.38 (d, 1H,
8.2 Hz), 7.81–7.83 (d, 1H, 7.8 Hz), 7.76–7.78 (d, 2H, 7.4 Hz), 7.47–
7.56 (m, 2H), 7.34–7.38 (t, 1H, 7.9 Hz), 4.05–4.10 (q, 2H, 7.1 Hz),
2.94–2.98 (t, 2H, 7.2 Hz), 2.40–2.44 (t, 2H, 7.2 Hz), 1.93–2.00 (m,
2H), 1.18–1.22 (t, 3H, 7.1 Hz); 13C NMR: d 172.96, 134.33, 134.02,
132.36, 129.12, 128.68, 128.36, 127.56, 126.66, 126.23, 125.89,
60.43, 34.05, 27.29, 25.35, 14.23; 77Se NMR: d 244.12; IR (CHCl3,
25.04, 17.64, 14.27; 77Se NMR: d 331.17; IR (CHCl3,
m
cmÀ1):
1732.1.
3.3.6. Ethyl 2-(5-methyl)pyridylselenobutanoate [(5-CH3C5H3N)Se
(CH2)3COOC2H5] (9c)
Yield 90%; yellow oil; 1H NMR: d 8.16 (s, 1H), 7.02–7.16 (m, 2H),
3.99–4.06 (q, 2H, 7.2 Hz), 3.08–3.13 (t, 2H, 6.9 Hz), 2.33–2.38 (t,
2H, 6.9 Hz), 2.18 (s, 3H), 1.94–2.05 (m, 2H), 1.15–1.20 (t, 3H,
7.2 Hz); 13C NMR: d 172.55, 151.19, 150.28, 136.53, 129.26,
128.95, 128.17, 125.29, 124.92, 60.03, 34.04, 25.74, 24.69, 17.68,
m
cmÀ1): 1735.8.
3.3.13. Ethyl 2-(diphenyl)methylselenoethanoate [(C6H5)2CHSeCH2-
COOC2H5] (12a)
14.33; 77Se NMR: d 326.41; IR (CHCl3,
m
cmÀ1): 1732.1.
Yield 92%; yellow oil; 1H NMR: d 7.35–7.38 (m, 4H), 7.09–7.23
(m, 6H), 5.58 (s, 1H), 3.99–4.11 (q, 2H, 7.2 Hz), 2.85 (s, 2H), 1.16–
1.24 (t, 3H, 7.2 Hz); 13C NMR: d 171.11, 140.57, 128.84, 128.57,
127.27, 60.93, 48.62, 24.40, 14.23; 77Se NMR: d 248.15; IR (CHCl3,
3.3.7. Ethyl 2-(5-bromo)pyridylselenoethanoate [(5-BrC5H3N)SeCH2-
COOC2H5] (10a)
Yield 82%; yellow oil; 1H NMR: d 8.39 (s, 1H), 7.48–7.55 (d, 1H,
8.4 Hz), 7.15–7.18 (d, 1H, 8.4 Hz), 4.04–4.11 (q, 2H, 6.9 Hz), 3.78 (s,
2H), 1.14–1.19 (t, 3H, 6.9 Hz); 13C NMR: d 169.76, 151.01, 138.41,
128.02, 125.70, 117.52, 61.15, 25.39, 14.04; 77Se NMR: d 358.71;
m
cmÀ1): 1730.8.
3.3.14. Ethyl 2-(diphenyl)methylselenopropanoate [(C6H5)2CHSe(CH2)2-
COOC2H5] (12b)
IR (CHCl3,
m
cmÀ1): 1732.0; MS-EI, m/e (R.I., assignment): 323
Yield 90%; yellow oil; 1H NMR: d 7.32–7.38 (m, 4H), 7.08–7.22
(m, 6H), 5.35 (s, 1H), 4.00–4.07 (q, 2H, 7.2 Hz), 2.44–2.56 (m,
4H), 1.14–1.20 (t, 3H, 7.2 Hz); 13C NMR: d 171.88, 141.43, 141.40,
128.93, 128.74, 128.57, 127.10, 60.47, 47.91, 35.12, 19.58, 14.34;
(100, [M]+), 321 (49, [(5-BrC5H3N)SeCH2COOCH2CH]+), 277 (33,
[(5-BrC5H3N)SeCH2CO]+).
3.3.8. Ethyl 2-(5-bromo)pyridylselenopropanoate [(5-BrC5H3N)Se
(CH2)2COOC2H5] (10b)
77Se NMR: d 241.12; IR (CHCl3, cmÀ1): 1735.8.
m
Yield 79%; yellow oil; 1H NMR: d 8.38 (s, 1H), 7.43–7.51 (d, 1H,
8.4 Hz), 7.13–7.16 (d, 1H, 8.4 Hz), 4.02–4.07 (q, 2H, 7.2 Hz), 3.13–
3.19 (t, 2H, 7.2 Hz), 2.40–2.44 (t, 2H, 7.2 Hz), 1.17–1.22 (t, 3H,
7.2 Hz); 13C NMR: d 171.03, 150.78, 137.74, 128.72, 125.68,
116.95, 60.38, 36.13, 25.27, 14.13; 77Se NMR: d 341.25; IR (CHCl3,
3.3.15. Ethyl 2-(diphenyl)methylselenobutanoate [(C6H5)2CHSe(CH2)3-
COOC2H5] (12c)
Yield 86%; yellow oil; 1H NMR:: d 7.25–7.30 (m, 4H), 7.15–7.18
(m, 6H), 5.43 (s, 1H), 4.01–4.08 (q, 2H, 7.2 Hz), 2.31–2.35 (t, 2H,
7.2 Hz), 2.22–2.26 (t, 2H, 7.2 Hz), 1.80–1.85 (m, 2H), 1.15–1.18 (t,
3H, 7.2 Hz); 13C NMR: d 171.46, 141.27, 128.88, 128.60, 128.54,
127.01, 60.35, 47.55, 35.08, 21.71, 19.22, 14.19; 77Se NMR: d
m
cmÀ1): 1731.4.
3.3.9. Ethyl 2-(5-bromo)pyridylselenobutanoate [(5-BrC5H3N)Se
(CH2)3COOC2H5] (10c)
238.11; IR (CHCl3, m
cmÀ1): 1732.0; MS-EI, m/e (R.I., assignment):
362 (100, [M+1]+), 361 (89, [M]+), 316 (84, [(C6H5)2CHSe(CH2)3-
CO]+), 167 (38, [(C6H5)2CH]+).
Yield 72%; yellow oil; 1H NMR: d 8.39 (s, 1H), 7.43–7.47 (d, 1H,
8.4 Hz), 7.11–7.13 (d, 1H, 8.1 Hz), 4.01–4.08 (q, 2H, 7.2 Hz), 3.11–
3.15 (t, 2H, 7.2 Hz), 2.33–2.38 (t, 2H, 7.2 Hz), 1.97–2.08 (m, 2H),
1.17–1.22 (t, 3H, 7.2 Hz); 13C NMR: d 172.06, 150.21, 136.14,
126.02, 125.47, 116.81, 60.11, 36.32, 24.98, 19.98, 14.09; 77Se
3.3.16. Ethyl 2-[(4-chlorophenyl)(phenyl)]methylselenoethanoate [(4-
ClC6H4)(C6H5)CHSeCH2COO C2H5] (13a)
Yield 89%; yellow oil; 1H NMR: d 7.30–7.34 (m, 4H), 7.11–7.24
(m, 5H), 5.56 (s, 1H), 4.02–4.09 (q, 2H, 6.9 Hz), 2.82 (s, 2H), 1.19–
1.23 (t, 3H, 6.9 Hz); 13C NMR: d 170.88, 140.17, 139.27, 133.27,
130.29, 128.84, 128.78, 127.57, 61.02, 47.81, 24.41, 14.34; 77Se
NMR: d 328.48; IR (CHCl3,
m
cmÀ1): 1730.7.
3.3.10. Ethyl 2-naphthylselenoethanoate [(1-C10H7)SeCH2COOC2H5]
(11a)
NMR: d 244.86; IR (CHCl3,
m
cmÀ1): 1728.4.
Yield 94%; greenish-yellow oil; 1H NMR: d 8.29–8.32 (d, 1H,
8.4 Hz), 7.82–7.84 (d, 1H, 7.2 Hz), 7.73–7.75 (d, 2H, 8.1 Hz), 7.39–
7.51 (m, 2H), 7.27–7.32 (t, 1H, 7.2 Hz), 3.88–3.95 (q, 2H, 7.2 Hz),
3.41 (s, 2H), 0.97–1.02 (t, 3H, 7.2 Hz); 13C NMR: d 171.95, 134.76,
133.94, 133.29, 129.03, 128.74, 128.64, 127.77, 126.58, 126.35,
3.3.17. Ethyl 2-[(4-chlorophenyl)(phenyl)]methylselenopropanoate
[(4-ClC6H4)(C6H5)CHSe(CH2)2C OOC2H5] (13b)
Yield 84%; yellow oil; 1H NMR: d 7.25–7.27 (m, 4H), 7.09–7.23
(m, 5H), 5.32 (s, 1H), 4.00–4.08 (q, 2H, 7.2 Hz), 2.45–2.56 (m,
4H), 1.15–1.20 (t, 3H, 7.2 Hz); 13C NMR: d 171.70, 141.11, 140.01,
133.01, 130.11, 128.79, 128.74, 127.37, 60.55, 47.19, 35.14, 19.72,
125.63, 60.81, 27.65, 14.08; 77Se NMR: d 269.19; IR (CHCl3,
m
cmÀ1): 1731.8; MS-EI, m/e (R.I., assignment): 311 (100, [M+18]+),
293 (7, [M]+), 292 (40, [MÀ1]+), 278 (16, [(1-C10H7)SeCH2-
COOCH2]+.
14.42; 77Se NMR: d 230.12; IR (CHCl3,
m
cmÀ1): 1739.7.
3.3.18. Ethyl 2-[(4-chlorophenyl)(phenyl)]methylselenobutanoate [(4-
ClC6H4)(C6H5)CHSe(CH2)3C OOC2H5] (13c)
3.3.11. Ethyl 2-naphthylselenopropanoate [(1-C10H7)Se(CH2)2COOC2-
H5] (11b)
Yield 82%; yellow oil; 1H NMR: d 7.27–7.31 (m, 4H), 7.12–7.23
(m, 5H), 5.26 (s, 1H), 3.98–4.05 (q, 2H, 7.2 Hz), 2.32–2.38 (t, 2H,
7.2 Hz), 2.23–2.28 (t, 2H, 7.2 Hz), 1.79–1.84 (m, 2H), 1.15–1.19 (t,
3H, 7.2 Hz); 13C NMR: d 172.46, 141.12, 140.25, 132.94, 130.10,
128.75, 128.70, 127.30, 60.26, 46.94, 34.15, 25.21, 25.11, 14.43;
Yield 81%; greenish-yellow oil; 1H NMR: d 8.38–8.41 (d, 1H,
8.4 Hz), 7.81–7.83 (d, 1H, 7.4 Hz), 7.78–7.80 (d, 2H, 7.8 Hz), 7.47–
7.56 (m, 2H), 7.33–7.37 (t, 1H, 7.1 Hz), 4.05–4.10 (q, 2H, 7.1 Hz),
3.09–3.12 (t, 2H, 7.4 Hz), 2.63–2.67 (t, 2H, 7.4 Hz), 1.18–1.21 (t,
3H, 7.1 Hz); 13C NMR: d 172.17, 134.48, 134.01, 133.35, 128.83,
77Se NMR: d 228.50; IR (CHCl3,
m
cmÀ1): 1732.5.