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References and notes
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(b) Usugi, S.-I.; Yorimitsu, H.; Shinokubo, H.; Oshima,
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16. For intramolecular examples: (a) Snider, B. B.; Buckman,
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18. Typical experimental procedure: Synthesis of a-iodocyc-
lodecane-2,6-dione 13: A solution of HgOyellow (4.5 mmol,
960 mg), I2 (4.0 mmol, 1020 mg) and 13 (1.49 mmol,
250 mg) in 50 mL of CCl4 was irradiated by 500 W
tungsten lamp and stirred at 0 ꢁC for 2 h. The reaction
mixture was filtered over Celiteꢂ and the filter cake was
washed with CH2Cl2 (2 · 20 mL). Filtrates were combined
and washed with satd Na2S2O3 (3 · 20 mL). The organic
layer was dried over MgSO4 and evaporated under
reduced pressure. The compound 13 was obtained as
yellow oil (400 mg) in 93% yield. Experimental data: 1H
NMR (500 MHz, CDCl3) d (ppm): 1.31–1.43 (m, 1H),
1.60–1.76 (m, 3H), 1.75–2.06 (m, 1H), 2.07–2.16 (m, 2H),
2.24 (dddd, 1H, 2J = 15.4, 3J = 11.5, 3J = 6.7, 3J = 4.7 Hz),
6. (a) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54,
´
3321–3354; (b) Molander, G. A.; Huerou, Y. L.; Brown,
G. A. J. Org. Chem. 2001, 66, 4511–4516.
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A.; Marko, I. E. Bull. Soc. Chim. Belg. 1997, 106, 297; (b)
Marko, I. E.; Ates, A. Synlett 1999, 7, 1033.
8. (a) Akgun, E.; Pindur, U. Synthesis 1984, 227–228; (b)
Pindur, U.; Muller, J.; Flo, C.; Witzel, H. Chem. Soc. Rev.
1987, 16, 75–87.
9. Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37,
3899.
10. Suginome, H.; Kondoh, T.; Gogonea, C.; Singh, V.; Goto,
H.; Osawa, E. J. Chem. Soc., Perkin Trans. 1 1995, 69–81.
11. Conception, J. I.; Francisco, C. G.; Hernandes, R.;
Salazar, J. A.; Suarez, E. Tetrahedron Lett. 1984, 25,
1953–1955.
12. McDonald, C. E.; Holcomb, H.; Leathers, T.; Ampadu-
Nyarko, F.; Frommer, J. Tetrahedron Lett. 1990, 31,
6283–6286.
3
3
2.34 (ddd, 1H, 2J = 14.4, J = 5.8, J = 5.8 Hz), 2.44 (ddd,
1H, 2J = 14.4, 3J = 7.0, 3J = 7.0 Hz), 2.58 (ddd, 1H,
2J = 16.4, 3J = 9.7, 3J = 4.4 Hz), 2.57 (m, 2H), 4.43 (dd,
1H, 3J = 11.5, 3J = 3.3). 13C NMR (125 MHz, CDCl3) d
(ppm): 19.70 (CH2), 22.30 (CH2), 27.22 (CH2), 31.81
(CH), 34.69 (CH2), 34.98 (CH2), 40.32 (CH2), 43.78
(CH2), 206.64 (C@O), 213.23 (C@O). EI-MS (70 eV),
m/z (%): 294 (4) [M+], 167 (100) [M+ÀI], 149 (58), 139 (26),
125 (37), 121 (44), 97 (60), 55 (57).
13. (a) Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.;
Quesnel, Y.; Marko, I. E. Tetrahedron Lett. 1999, 40,