M. D. Otero et al. / Tetrahedron 60 (2004) 4609–4612
4611
94–96 8C. IR (KBr) n(cm21): 2971, 2154, 1689, 1367,
1062, 1007, 854. H NMR (300 MHz, CDCl3) d: 1.23 (s,
9H), 4.53 (s, 2H). 13C NMR (75.4 MHz, CDCl3) d: 26.8,
27.2, 37.9, 102, 210. MS m/e (relative intensity) EI: 205
(Mþþ4, 2), 203 (Mþþ2, 1), 85 (6), 57 (100). Anal. Calcd
for C7 H11 N O Se: C, 40.97; H, 5.36. Found: C, 41.17; H, 5.41.
167 (25), 152 (71), 105 (72), 77 (61), 51 (28). Anal. Calcd
for C22H18O2Se: C, 67.18; H, 4.58. Found: C, 66.90; H,
4.69.
1
3.1.9. 2-(3,3-Dimethyl-2-oxo-butylseleno)acetophenone
(2f). 40% yield. Mp 41–43 8C. IR (NaCl) n(cm21): 3052,
2955, 2928, 1724, 1668, 1595, 1275, 1055. 1H NMR
(300 MHz, CDCl3) d: 1.21 (s, 9H), 3.64 (s, 2H), 3.94 (s,
2H), 7.47 (t, 2H, J¼7.6 Hz), 7.57 (t, 1H, J¼7.6 Hz), 7.96 (d,
2H, J¼7.6 Hz). 13C NMR (75.4 MHz, CDCl3) d: 26.9, 27.8,
28.7, 128.5, 128.6, 133.2, 135.0, 194.8, 209.8. MS m/e
(relative intensity) EI: 298 (Mþþ4, 6), 296 (Mþþ2, 3), 294
(Mþ, 1), 217 (17), 149 (8), 120 (17), 105 (94), 91 (37), 77
(52), 57 (100), 51 (20). Anal. Calcd for C14 H18O2Se: C,
56.56; H, 6.06. Found: C, 56.51; H, 5.89.
3.1.4. 2-(Phenacylseleno)acetophenone (2a). 63% yield.
Mp 67–69 8C. IR (KBr) n(cm21): 3060, 2960, 1672, 1595,
1279, 1184, 750, 684. 1H NMR (300 MHz, CDCl3) d: 4.0 (s,
4H), 7.40–7.60 (m, 6H), 8.0 (d, 4H, J¼7 Hz). 13C NMR
(75.4 MHz, CDCl3) d: 28.9, 128.8, 133.6, 135.3, 195.0. MS
m/e (relative intensity) EI: 315 (Mþþ4, 4), 316 (Mþþ2, 2),
314 (Mþ, 1), 237 (38), 105 (100), 91 (20), 77 (50), 51 (15).
Anal. Calcd for C16H14O2Se: C, 60.57; H, 4.42. Found: C,
60.45; H, 4.60.
3.1.5. 2-(4-Methoxy-phenacylseleno)acetophenone (2b).
57% yield. Mp 48–50 8C. IR (NaCl) n(cm21): 3061, 2960,
2839, 1665, 1598, 1275, 1173. 1H NMR (300 MHz, CDCl3)
d: 3.86 (s, 3H), 3.95 (s, 2H), 3.98 (s, 2H), 6.93 (d, 2H,
J¼8 Hz), 7.46 (t, 2H, J¼7.5 Hz), 7.57 (t, 1H, J¼7.5 Hz),
7.9–8.0 (m, 4H). 13C NMR (75.4 MHz, CDCl3) d: 28.8,
55.7, 114.1, 128.5, 128.9, 129.0, 131.3, 133.6, 135.5, 164.0,
194.0, 195.3. MS m/e (relative intensity) EI: 348 (Mþþ4,
2), 346 (Mþþ2, 1), 267 (23), 187 (4), 150 (17), 135 (100),
121 (17), 105 (22), 91 (8), 77 (30), 51 (8). Anal. Calcd for
C17H16O3Se: C, 58.79; H, 4.61. Found: C, 59.04; H, 4.58.
Acknowledgements
This study was financed by the Spanish Ministry of Science
and Technology (BQU2001-1083). B. Batanero thanks to
this Ministry for the ‘Ramon y Cajal’ financiation.
References and notes
¨
1. Lowig, C. J. Pogg. Ann. 1836, 37, 552.
2. Sevrin, M.; Van Ende, D.; Krief, A. Tetrahedron Lett. 1976,
2643.
3.1.6. 2-(4-Chloro-phenacylseleno)acetophenone (2c).
42% yield. Mp 62–64 8C. IR (KBr) n(cm21): 3060, 2923,
1668, 1589, 1338, 1276, 1091. 1H NMR (300 MHz, CDCl3)
d: 3.95 (s, 2H), 3.98 (s, 2H), 7.4–7.6 (m, 5H) 7.86–8.0 (m,
4H). 13C NMR (75.4 MHz, CDCl3) d: 28.7, 29.0, 128.9,
129.0, 129.2, 129.9, 130.3, 133.7, 135.4, 140.1, 193.9,
195.1. MS m/e (relative intensity) EI: 354 (Mþþ6, 3), 352
(Mþþ4, 7), 350 (Mþþ2, 3), 237 (140), 154 (177), 156 (73),
141 (269), 139 (803), 113 (113), 11 (34), 105 (1000), 91
(172), 77 (496), 51 (177). Anal. Calcd for C16H13ClO2 Se:
C, 54.62; H, 3.7. Found: C, 54.77; H, 3.90.
3. Seebach, D.; Beck, A. K. Angew. Chem. Int. Ed. Engl. 1974,
13, 806.
4. Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Russel,
C. G.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102,
4438.
5. Sharpless, K. B.; Young, M. W. J. Org. Chem. 1975, 40, 947.
6. Halazy, S.; Krief, A. Tetrahedron Lett. 1979, 4233.
7. Sevrin, M.; Dumont, W.; Hevesi, L.; Krief, A. Tetrahedron
Lett. 1976, 2647.
8. Sevrin, M.; Krief, A. J. Chem. Soc., Chem. Commun. 1980,
656.
3.1.7. 2-(4-Bromo-phenacylseleno)acetophenone (2d).
62% yield. Mp 34–36 8C. IR (NaCl) n(cm21): 3057,
2923, 1666, 1583, 1272, 1070, 1004. H NMR (300 MHz,
9. Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Vemura, S. J.
J. Chem. Soc. Perkin Trans. 1 1995, 2871.
1
10. Fukuzawa, S.; Tsudzuki, K. Tetrahedron: Asymmetry 1995, 6,
1039.
CDCl3) d: 3.94 (s, 2H), 3.98 (s, 2H), 7.47 (t, 2H, J¼7.4 Hz)
7.55–7.63 (m, 3H), 7.83 (d, 2H, J¼8.5 Hz), 7.95 (d, 2H,
J¼7.4 Hz). 13C NMR (75.4 MHz, CDCl3) d: 28.8, 29.2,
128.9, 129.0, 130.4, 132.2, 133.8, 134.2, 135.4, 194.0,
194.9. MS m/e (relative intensity) EI: 398 (Mþþ6, 15), 396
(Mþþ4, 21), 394 (Mþþ2, 9), 392 (Mþ, 3), 317 (161), 315
(156), 185 (248), 183 (250), 157 (106), 155 (109), 105
(1000), 91 (192), 77 (521), 51 (264). Anal. Calcd for
C16H13BrO2Se: C, 48.48; H, 3.28. Found: C, 48.31; H, 3.43.
11. Wirth, T. Tetrahedron Lett. 1995, 36, 7849.
12. Davies, M. K.; Durrant, M. C.; Levason, W.; Reid, G.;
Richards, R. L. J. Chem. Soc., Dalton Trans. 1999, 1077.
13. Engman, L.; Anderson, C.; Morgenstern, R.; Cotgreave, I. A.;
Andersson, C. M.; Hallberg, A. Tetrahedron 1994, 50, 2929.
14. Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347.
15. Engman, L.; Tunek, A.; Hallberg, M.; Hallberg, A. Chem.
Biol. Interact. 1994, 93, 129.
16. Comprehensive organometallic chemistry II; Abel, F. W.,
Stone, F. G. A., Wilkinson, G., McKillop, A., Eds.; Pergamon:
Oxford, 1995; Vol. II, p 516.
3.1.8. 2-(4-Phenyl-phenacylseleno)acetophenone (2e).
64% yield. Mp 37–39 8C. IR (NaCl) n(cm21): 3060,
1667, 1599, 1274, 1181. H NMR (300 MHz, CDCl3) d:
4.0 (s, 2H), 3.02 (s, 2H), 7.40–7.50 (m, 5H), 7.53–7.70 (m,
5H), 7.95–8.1 (m, 4H). 13C NMR (75.4 MHz, CDCl3) d:
28.9, 127.5, 127.6, 128.5, 128.9, 129.2, 129.5, 133.7, 134.2,
135.5, 139.9, 146.4, 194.8, 195.2. MS m/e (relative
intensity) EI: 396 (Mþþ6, 1), 394 (Mþþ4, 3), 392
(Mþþ2, 1), 390 (Mþ, 1), 313 (25), 196 (24), 181 (100),
1
17. Houben-Weyl Methoden der Organischen Chemie;
Rheinboldt, H., Mueller, E., Eds.; Georg Thieme: Stuttgart,
1955; Vol. IX, p 972.
18. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.;
Montanucci, M. J. Org. Chem. 1983, 48, 4289.
19. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976,
41, 1485.