V. Saravanan et al. / Tetrahedron Letters 45 (2004) 681–683
683
to )78 ꢁC. (Et4N)2WSe4, 1, (1.13 g, 1.5 mmol) was added
References and notes
at once. The reaction mixture was allowed to warm to
room temperature and stirred for another half an hour.
The solvent was removed under reduced pressure and
the black residue was extracted with CH2Cl2–Et2O (3:7,
6 · 15 mL) and filtered through a Celite pad. The filtrate
was concentrated and the crude product was purified by
recrystallisation or column chromatography on silica
gel.
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Method B: POCl3 was used as the promoter instead of
(COCl)2.
2.2. Data for selected compounds
1-(Selenopivaloyl)pyrrolidine (6) yield 91%, yellow
1
crystals, mp 43–45 ꢁC; IR (KBr) 1510 (C@Se) cmꢀ1; H
NMR (300 MHz, CDCl3) d 1.41 (s, 9H, 3 ꢁ CH3), 1.89
(quint, J ¼ 6:6 Hz, 2H, CH2), 2.05 (quint, J ¼ 6:6 Hz,
2H, CH2), 3.66 (t, J ¼ 6:6 Hz, 2H, CH2), 3.94 (t,
J ¼ 6:6 Hz, 2H, CH2); 13C NMR (CDCl3, 75 MHz) 23.1,
27.5, 30.9, 46.0, 54.2, 62.4, 213.9; 77Se NMR (CDCl3,
77 MHz) 631.9; MS (EI) m=z 219 [Mþ]; HRMS, calcd
for C9H17NSe: 220.0604 [M+H]þ, found: 220.0585.
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4-(Pyrrolidine-1-carboselenoyl)benzoic acid benzyl ester
(8) yield 79%; yellow crystals; mp 106–108 ꢁC; IR (KBr)
1
1513 (C@Se), 1715 (C@O) cmꢀ1; H NMR (300 MHz,
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CDCl3) d 2.04 (quint, J ¼ 6:6 Hz, 2H, CH2), 2.13 (quint,
J ¼ 6:6 Hz, 2H, CH2), 3.28 (t, J ¼ 6:6 Hz, 2H, CH2),
3.95 (t, J ¼ 6:6 Hz, 2H, CH2), 5.37 (s, 2H, CH2), 7. 34–
7.45 (m, 7H, Ar) 8.53 (d, J ¼ 7:8 Hz, 2H, Ar); 13C NMR
(CDCl3, 75 MHz) 24, 26.5, 54.5, 56.9, 66.8, 124.5, 128.1,
128.3, 128.6, 129.7, 129.9, 135.8, 150.6, 165.7, 179.2; 77Se
NMR (CDCl3, 77 MHz) 744.5; MS (EI) m=z 373 [Mþ];
HRMS, calcd for C18H17NO2Se: 396.0479 [M+Na]þ,
found: 396.0483.
9. Ming, D.; Zhang, P.-F.; Tao, Y.; Fan, W.-Q. Synth.
Commun. 1996, 26, 2617–2623.
1-Selenoacetylpiperidine-4-one (9) yield 55%; yellow
crystals; mp 82–84 ꢁC; IR (KBr) 1481 (C@Se), 1723
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2001, 42, 5949–5951; (b) Bethke, J.; Karaghiosoff, K.;
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1
(C@O) cmꢀ1; H NMR (300 MHz, CDCl3 ) d 2.63 (t,
J ¼ 6:6 Hz, 2H, CH2), 2.73 (t, J ¼ 6:6 Hz, 2H, CH2),
2.76 (s, 3H, CH3), 4.02 (t, J ¼ 6:6 Hz, 2H, CH2), 4.62
(t, J ¼ 6:6 Hz, 2H, CH2); 13C NMR (CDCl3, 75 MHz)
37.0, 39.3, 39.5, 47.5, 52.4, 204.2, 204.6; 77Se NMR
(CDCl3, 77 MHz) 667.8; MS (EI) m=z 205 [Mþ], HRMS,
calcd for C7H11NOSe: 206.0084 [M+H]þ, found:
206.0096.
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11163–11176; (b) Cava, M. P.; Saris, L. A. J. Chem. Soc.,
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€
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955; (b) OÕNeal, S.; Kolis, J. W. J. Am. Chem. Soc. 1988,
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Acknowledgements
The authors thank the Department of Science and
Technology, New Delhi for financial support.