M. Jiang, M. Shi / Tetrahedron 65 (2009) 798–801
801
122.5, 127.9, 128.0, 129.0, 129.1, 129.6, 132.4, 135.3, 135.6, 136.2,
196.3; MS (EI) m/z (%): 394 (29.44) [Mþ], 366 (3.76), 239 (13.35), 211
(98.19), 209 (49.75), 183 (90.98), 157 (100.00), 77 (50.50); HRMS
(EI) calcd for C17H15OBrSe (Mþ) requires: 393.9471, found:
393.9484.
143.3,145.2,197.8; MS (EI) m/z (%): 330 (22.39) [Mþ], 302 (4.02), 211
(34.52), 173 (15.39), 130 (42.34), 119 (83.12), 91 (100.00), 77 (19.20);
HRMS (EI) calcd for C18H18OSe (Mþ) requires: 330.0523, found:
330.0510.
Acknowledgements
4.2.7. (2-Chlorophenyl)(1-(phenylselanyl)cyclobutyl)-
methanone (4g)
Financial support from the Shanghai Municipal Committee of
Science and Technology (06XD14005 and 08dj1400100-2), National
Basic Research Program of China (973)-2009CB825300, and the
National Natural Science Foundation of China (20872162,
20672127, and 20732008) are greatly acknowledged.
A colorless oil; IR (CH2Cl2):
1281, 1242,1050, 1022, 968, 898, 739, 691 cmꢁ1; 1H NMR (300 MHz,
CDCl3, TMS): 1.88–1.96 (1H, m, CH2), 2.12–2.24 (2H, m, CH2), 2.34–
n 3058, 2950, 2852, 1681, 1477, 1436,
d
2.43 (1H, m, CH2), 2.71–2.82 (2H, m, CH2), 7.21–7.44 (6H, m, ArH),
7.51 (2H, d, J¼8.4 Hz, ArH), 7.78 (1H, d, J¼9.0 Hz, ArH); 13C NMR
(75 MHz, CDCl3, TMS):
d 16.1, 32.1, 54.4, 126.2, 128.3, 128.9, 129.0,
Supplementary data
129.3, 130.4, 130.8, 131.5, 135.8, 137.4, 200.6; MS (EI) m/z (%): 350
(8.29) [Mþ], 315 (79.95), 287 (10.50), 211 (50.30), 183 (13.88), 157
(21.35), 139 (100.00), 77 (30.72); HRMS (EI) calcd for C17H15OClSe
(Mþ) requires: 349.9977, found: 349.9970.
1H and 13C NMR spectroscopic charts for compounds 4a–4j are
provided. This material is available free of charge via the Internet.
Supplementary data associated with this article can be found in the
4.2.8. (p-Tolyl)(1-(phenylselanyl)cyclobutyl)methanone (4h)
A colorless oil; IR (CH2Cl2):
1391, 1246, 1219, 1121, 775, 696 cmꢁ1
TMS): 1.81–1.90 (1H, m, CH2), 2.31–2.49 (3H, m, CH2), 2.40 (3H, s,
n
3065, 2957, 2853, 1686, 1594, 1449,
References and notes
;
1H NMR (300 MHz, CDCl3,
1. (a) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104, 6255–6286; (b)
Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125–2180; (c)
Parnham, M. J.; Graf, E. Prog. Drug Res. 1991, 36, 9–11; (d) Nogueira, C. W.;
Quinhones, E. B.; Jung, E. A. C.; Zeni, G.; Rocha, J. B. T. Inflamm. Res. 2003, 52,
56–59.
2. (a) Huguet, J. L. Adv. Chem. Ser. 1967, 345–349; (b) Sharpless, K. B.; Young, M.
W.; Lauer, R. F. Tetrahedron Lett. 1973, 22, 1979–1982.
3. (a) Reich, H. J. J. Org. Chem. 1975, 40, 2570–2572; (b) Sharpless, K. B.; Lauer, R. F.
J. Am. Chem. Soc. 1972, 94, 7154–7155.
4. (a) Nicolaou, K. C.; Petasis, N. A. Selenium in Natural Products Synthesis; CIS:
Philadelphia, 1984; (b) Paulmier, C. Selenium Reagents and Intermediates in
Organic Synthesis; Pergamon: Oxford, 1986; (c) Patai, S.; Rappoport, Z. The
Chemistry of Organic Selenium and Tellurium Compounds; Wiley: New York, NY,
1986; Vol. 1; (d) Liotta, D. Organoselenium Chemistry; Wiley: New York, NY,
1987; (e) Krief, A.; Hevesi, L. Organoselenium Chemistry I; Springer: Berlin, 1988;
(f) Back, T. G. Organoselenium Chemistry: A Practical Approach; Oxford University
Press: Oxford, 1999; (g) Reich, H. J. Acc. Chem. Res. 1979, 12, 22–30; (h) Liotta, D.
Acc. Chem. Res. 1984, 17, 28–34; (i) Wirth, T. Topics in Current Chemistry;
Springer: Heidelberg, 2000; Vol. 208; (j) Mugesh, G.; Singh, H. B. Acc. Chem. Res.
2002, 35, 226–236.
d
CH3), 2.79–2.88 (2H, m, CH2), 7.20–7.35 (5H, m, ArH), 7.41 (2H, d,
J¼7.8 Hz, ArH), 7.82 (2H, d, J¼7.8 Hz, ArH); 13C NMR (75 MHz, CDCl3,
TMS):
d 16.2, 21.6, 33.1, 53.3, 128.3, 128.81, 128.84, 128.87, 129.6,
131.1, 136.1, 143.3, 197.7; MS (EI) m/z (%): 330 (19.21) [Mþ], 302
(4.74), 252 (6.19), 211 (39.99), 173 (23.83), 119 (100.00), 91 (75.29),
77 (22.51); HRMS (EI) calcd for C18H18OSe (Mþ) requires: 330.0523,
found: 330.0517.
4.2.9. (4-Ethylphenyl)(1-(phenylselanyl)cyclobutyl)methanone (4i)
A colorless oil; IR (CH2Cl2):
1436, 1281, 1242, 1208, 1050, 968, 898, 739, 691 cmꢁ1
(300 MHz, CDCl3, TMS):
n
3058, 1987, 2852, 1681, 1589, 1477,
;
1H NMR
d
1.26 (3H, t, J¼7.8 Hz, CH3), 1.83–1.87 (1H,
m, CH2), 2.33–2.46 (3H, m, CH2), 2.70 (2H, q, J¼7.8 Hz, CH2), 2.80–
2.87 (2H, m, CH2), 7.23–7.33 (5H, m, ArH), 7.42 (2H, d, J¼7.2 Hz,
ArH), 7.85 (2H, d, J¼7.2 Hz, ArH); 13C NMR (75 MHz, CDCl3, TMS):
5. Shi, M.; Wang, B.-Y.; Li, J. Eur. J. Org. Chem. 2005, 759–765.
6. Shi, M.; Lu, J.-M. Synlett 2005, 2352–2356.
d
15.1, 16.2, 28.9, 33.1, 53.3, 127.7, 128.3, 128.8, 128.9, 129.7, 131.3,
7. For the synthesis of MCBs, see: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589–636.
8. It has been reported that treatment of diphenyl diselenide with iodosobenzene
diacetate produces an electrophilic selenenylating agent for double bonds. See:
(a) Tingoli, M.; Tiecco, M.; Testaferri, L.; Temperini, A. Synth. Commun. 1998, 28,
1769–1772; (b) Tiecco, M.; Tingoli, M.; Testaferri, L. Pure Appl. Chem. 1993, 65,
715–722 and references cited therein; (c) Miyoshi, N.; Takai, Y.; Murai, S.; So-
noda, N. Bull. Chem. Soc. Jpn. 1978, 51, 1265–1266; (d) Brugier, D.; Outurquin, F.;
Paulmier, C. J. Chem. Soc., Perkin Trans. 1 2001, 37–43.
9. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434–5449.
10. Chen, D.-W.; Chen, Z.-C. Tetrahedron Lett. 1994, 41, 7637–7638.
11. The examples of water as nucleophilic reagent: (a) Kurz, J. L.; Lu, J. Y. J. Phys.
Chem. 1983, 87, 1444–1448; (b) Chi, D. Y.; Kim, D. W.; Hong, D. J.; Kim, H. S.
J. Org. Chem. 2004, 69, 3186–3189.
136.2, 149.4, 197.8; MS (EI) m/z (%): 344 (20.76) [Mþ], 314 (9.52), 211
(35.37), 187 (20.84), 171 (9.47), 157 (27.23), 133 (100.00), 77 (46.26);
HRMS (EI) calcd for C19H20OSe (Mþ) requires: 344.0679, found:
344.0689.
4.2.10. (m-Tolyl)(1-(phenylselanyl)cyclobutyl)methanone (4j)
A colorless oil; IR (CH2Cl2):
1391, 1246, 1219, 1121, 775, 696 cmꢁ1
TMS): 1.83–1.92 (1H, m, CH2), 2.32–2.51 (3H, m, CH2), 2.38 (3H, s,
n
3065, 2957, 2853, 1686, 1594, 1449,
;
1H NMR (300 MHz, CDCl3,
d
CH3), 2.79–2.88 (2H, m, CH2), 7.23–7.36 (5H, m, ArH), 7.42 (2H, d,
12. The oxidation of iodobenzene diacetate: (a) Swenton, J. S.; Callinan, A.; Chen, Y.;
Rohde, J. J.; Kerns, M. L.; Morrow, J. W. J. Org. Chem. 1996, 61, 1267–1274; (b)
Canesi, S.; Bouchu, D.; Ciufolini, M. A. Org. Lett. 2005, 7, 175–177.
J¼7.8 Hz, ArH), 7.70 (2H, s, ArH); 13C NMR (75 MHz, CDCl3, TMS):
d
16.2, 21.6, 33.1, 53.3, 121.0, 128.3, 128.8, 128.9, 129.6, 131.1, 136.1,