4-Nitrophenyl methyl ketone (5r)20. Yellow solid; mp 80–81 ◦C;
1H NMR (400 MHz, CDCl3): d = 8.30 (d, J = 8.8 Hz, 2H), 8.10
(d, J = 8.8 Hz, 2H), 2.67 (s, 3H); 13C NMR (100 MHz, CDCl3):
d = 196.31, 150.31, 141.32, 129.27, 123.92, 26.95.
Cycloocta-2,7-dienone22. Colorless
(400 MHz, CDCl3): d 6.23–6.37 (m, 4H), 2.31–2.37 (m,
4H), 1.69–1.76 (m, 2H); 13C NMR (100 MHz, CDCl3): d 193.40,
141.57, 135.79, 27.06, 24.90.
liquid;
1H
NMR
◦
1
9,10-Anthraquinone (5s)12. Yellow solid; mp 275–277 C; H
NMR (400 MHz, CDCl3): d = 8.32–8.34 (m, 4H), 7.81–7.83 (m,
4H); 13C NMR (100 MHz, CDCl3): d = 183.15, 134.11, 133.52,
127.23.
Adamantane-1,3-diol24. White solid; mp 298–300 ◦C;1H NMR
(400 MHz, DMSO-d6): d 4.49 (s, 2H), 2.12 (s, 2H), 1.46–1.90 (m,
10H), 1.37 (s, 2H); 13C NMR (100 MHz, DMSO-d6): d 68.49,
53.21, 44.01, 34.67, 30.62.
4-Acetoxy-1-tetralone (5t)12. Slightly yellow oil; 1H NMR
(400 MHz, CDCl3): d = 8.01 (d, J = 8.0 Hz, 1H), 7.54 (t, J =
7.6 Hz, 1H), 7.40–7.44 (m, 2H), 6.10 (t, J = 4.6 Hz, 1H), 2.86–
2.94 (m, 1H), 2.60–2.67 (m, 1H), 2.23–2.41 (m, 2H), 2.09 (s, 3H);
13C NMR (100 MHz, CDCl3): d = 196.55, 170.22, 140.52, 133.71,
131.77, 128.81, 128.12, 126.94, 68.86, 34.18, 28.26, 21.00.
◦
1-Acetamidoadamantane25. White solid; mp 147–149 C;1H
NMR (400 MHz, CDCl3): d 5.32 (s, 1H), 2.04 (s, 3H), 1.97 (s,
6H), 1.90 (s, 3H), 1.65 (s, 6H); 13C NMR (100 MHz, CDCl3): d
169.44, 51.86, 41.49, 36.25, 29.32, 24.57. IR (KBr): n = 3278, 3079,
2906, 2847, 1643, 1559, 1373, 1361, 1342, 1304, 1138 cm-1. HRMS
(ESI): m/z: calcd. for C12H19ONa [M + Na]+: 216.1359; found:
216.1363.
2¢-Chloro-3¢,4¢-dihydro-2¢H-spiro[[1,3]dioxolane-2,1¢-naphtha-
lene] (5u). Colorless liquid; 1HNMR(400MHz, CDCl3): d = 8.03
(d, J = 7.6 Hz, 1H), 7.64–7.68 (m, 2H), 7.50–7.53 (m, 1H), 4.56–
4.59 (m, 1H), 4.25–4.33 (m, 4H), 3.40 (dd, J = 3.6 Hz, 17.6 Hz, 1H),
3.24 (dd, J = 3.6 Hz, 17.6 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d = 193.24, 140.42, 134.42, 131.34, 129.70, 127.14, 125.48, 105.92,
Acknowledgements
This work was financially supported by The National Natural
Science Foundation of China (No. 20572046 and No. 20872064),
Program for New Century Excellent Talents in University (NCET-
07-0461), and the Tianjin Natural Science Foundation (09JCY-
BJC05900).
˜
67.00, 64.40, 59.14, 45.13; IR (KBr): n = 2958, 2923, 2871, 2852,
1733, 1697, 1601, 1490, 1456, 1435, 1288, 1079, 969, 767 cm-1.
HRMS (ESI): m/z: calcd. for C12H11ClO3H [M + H]+ 239.0469;
found: 239.0474.
Isobenzofuran-1-one (5v)12. White solid; mp 68–69 ◦C; 1H
NMR (400 MHz, CDCl3): d = 7.83 (d, J = 7.6 Hz, 1H), 7.62
(t, J = 7.6 Hz, 1H), 7.43–7.47 (m, 2H), 5.25 (s, 2H); 13C NMR
(100 MHz, CDCl3): d = 171.03, 146.43, 133.93, 128.90, 125.54,
122.05, 69.58.
Notes and references
1 M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph No.
186, American Chemical Society, Washington DC, 1990.
2 For Cr-catalyzed oxidation, see: (a) J. Muzart, Tetrahedron Lett.,
1987, 28, 2131; (b) S. Yamazaki, Org. Lett., 1999, 1, 2129. For Mn-
catalyzed oxidation, see: (c) N. H. Lee, C.-S. Lee and D. S. Jung,
Tetrahedron Lett., 1998, 39, 1385. For Ru-catalyzed oxidation, see:
(d) S-I. Murahashi, Y. Oda, T. Naota and T. Kuwabara, Tetrahedron
Lett., 1993, 34, 1299; (e) S. I. Murahashi, N. Komiya, Y. Oda, T.
Kuwabara and T. Naota, J. Org. Chem., 2000, 65, 9186. For Rh-
catalyzed oxidation, see: (f) A. J. Catino, J. M. Nichols, H. Choi,
S. Gottipamula and M. P. Doyle, Org. Lett., 2005, 7, 5167. For Fe-
catalyzed oxidation, see: (g) C. Pavan, J. Legros and C. Bolm, Adv.
Synth. Catal., 2005, 347, 703; (h) M. Nakanishi and C. Bolm, Adv.
Synth. Catal., 2007, 349, 861. For Bi-catalyzed oxidation, see: (i) J.
Oldham, A. J. Burton and A. G. Barrett, Org. Lett., 2005, 7, 4549. For
Ni-catalyzed oxidation, see: (j) S. Yamazaki, Synth. Commun., 1999,
29, 2211. For Cu-catalyzed oxidation, see: (k) S. Velusamy and T.
Punniyamurthy, Tetrahedron Lett., 2003, 44, 8955. For Co-catalyzed
oxidation, see: (l) T. Punniyamurthy and J. Iqbal, Tetrahedron Lett.,
1994, 35, 4003; (m) P. Li and H. Alper, J. Mol. Catal., 1990, 61, 51.
For Au-catalyzed oxidation, see: (n) H.-R. Li, Z.-P. Li and Z.-J. Shi,
Tetrahedron, 2009, 65, 1856. For Mo-catalyzed oxidation, see: (o) S.
Das, T. Bhowmick, T. Punniyamurthy, D. Dey, J. Nath and M. K.
Chaudhuri, Tetrahedron Lett., 2003, 44, 4915.
3 (a) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; (b) A.
Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press:
London, 1997; (c) A. Varvoglis, Tetrahedron, 1997, 53, 1179; (d) T.
Wirth, Hypervalent Iodine Chemistry: Modern Developments in Organic
Synthesis; Topics in Current Chemistry Series 224; Springer: Berlin-
Tokyo, 2003; (e) T. Wirth, Angew. Chem., Int. Ed., 2005, 44, 3656;
(f) R. D. Richardson and T. Wirth, Angew. Chem., 2006, 118, 4510,
(Angew. Chem., Int. Ed., 2006, 45, 4402); (g) V. V. Zhdankin and P. J.
Stang, Chem. Rev., 2008, 108, 5299–5358; (h) V. V. Zhdankin, Arkivoc,
2009, i, 1–62; (i) M. Ochiai and K. Miyamoto, Eur. J. Org. Chem.,
2008, 4229; (j) T. Dohi and Y. Kita, Chem. Commun., 2009, 2073;
(k) M. Uyanik and K. Ishihara, Chem. Commun., 2009, 2086.
The typical procedure for the IBS-catalyzed alkane C–H oxidation
To the suspension of 1b (0.05 mmol, 15.3 mg), Bu4NHSO4
R
(0.2 mmol, 67.8 mg), and Oxoneꢀ (3 mmol, 1.84 g) in CH3CN (4
mL) in a two necked round-bottom flask equipped with condenser
and magnetic stirrer bar was added cyclohexane (4 mL, 33 mmol).
The mixture was heated at 60 ◦C in an oil bath for 24 h. After
cooling to room temperature, the resulting mixture was filtered to
remove the undissolved solid. The filtrates were washed with water
(5 mL ¥ 2) and brine (5 mL), dried with anhydrous MgSO4. Then
the solution was subjected to GC analysis.
1
Cyclohept-2-enone21. Colorless liquid; H NMR (400 MHz,
CDCl3): d 6.52–6.58 (m, 1H), 5.96–5.99 (d, J = 12 Hz, 1H), 2.57–
2.59 (m, 2H), 2.41–2.44 (m, 2H), 1.77–1.83 (m, 4H); 13C NMR
(100 MHz, CDCl3): d 204.26, 146.35, 132.46, 43.46, 30.16, 26.06,
21.65.
Cyclohepta-2,6-dienone22. Colorless liquid; 1H NMR
(400 MHz, CDCl3): d 6.57–6.61 (m, 2H), 6.06 (d, J = 11.6 Hz,
2H), 2.42 (t, J = 3.2 Hz, 4H); 13C NMR (100 MHz, CDCl3): d
193.03, 143.94, 133.74, 27.26.
Cyclooct-2-enone23. Colorless liquid; 1H NMR (400 MHz,
CDCl3): d 6.30–6.36 (td, J = 12.8 Hz, 6.2 Hz, 1H), 5.97–6.00
(d, J = 12.8 Hz, 1H), 2.61–2.65 (t, J = 6.8 Hz, 2H), 2.47–2.51 (m,
2H), 1.76–1.83 (m, 2H), 1.52–1.64 (m, 2H); 13C NMR (100 MHz,
CDCl3): d 206.04, 141.63, 132.32, 42.63, 28.47, 25.00, 23.00, 23.49.
4 (a) K. C. Nicolaou, P. S. Baran and Y.-L. Zhong, J. Am. Chem. Soc.,
2001, 123, 3183; (b) K. C. Nicolaou, T. Montagnon, P. S. Baran and
Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245.
2264 | Org. Biomol. Chem., 2011, 9, 2258–2265
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