J. N. Moorthy et al. / Tetrahedron Letters 47 (2006) 1757–1761
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Acknowledgements
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33.
1. (a) Moorthy, J. N.; Singhal, N.; Mal, P. Tetrahedron Lett.
004, 45, 309; (b) Moorthy, J. N.; Singhal, N.; Venkata-
We thank the Department of Science and Technology,
India, for the financial support. N.S. is grateful to CSIR,
India, for a senior research fellowship.
1
1
2
krishnan, P. Tetrahedron Lett. 2004, 45, 5419.
2. For diverse reactions mediated by IBX, see: (a) Nicolaou,
K. C.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2001,
123, 3183; (b) Nicolaou, K. C.; Mathison, C. J. N.;
Montagnon, T. Angew. Chem., Int. Ed. 2003, 42, 4077; (c)
Nicolaou, K. C.; Baran, P. S. Angew. Chem., Int. Ed. 2002,
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13. Dalton, D. R.; Dutta, V. P.; Jones, D. C. J. Am. Chem.
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14. General procedure for the conversion of benzyl halides to
carbonyl compounds: In a typical experiment, 1–2 mmol
of the halide and 1.5–2.0 equiv of IBX in 1.0 mL of
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2
atmo-
5
sphere. After completion of the reaction as determined
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1
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(
4
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2
N atmosphere. The progress of the reaction was moni-
tored by TLC analysis. As soon as the starting material
disappeared, 3.0 equiv of IBX was introduced into the
same pot and the reaction mixture was heated at 60–70 °C.
After completion of the reaction, it was quenched with
water and extracted with ethyl acetate. The products were
purified by silica gel chromatography and characterized
spectroscopically.
1
1
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from GC analysis, regardless of whether the reaction was
run in freshly distilled DMSO or rigorously dried
DMSO. By employing more equivalents of IBX, the
yields of the oxidation products could be improved
in addition to reducing the reaction time (cf. Table 1,
entry 1).
2
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1
4