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1H NMR and can be further purified by flash chromatography over silica gel. (B) With allymercury bromide: The reaction was performed with identical procedure as above but by adding THAB (1mmol) together with allylmercury bromide (Immol) instead of diallylmercury.
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[7] For other examples about promoting nucleophilic reaction with quaternary ammonium catalyst see: (a) Masuyama, Y.; Kishida, M.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1995, 1405
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(e) Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662
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0344148449
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[8] The ease of allylation of the ketone carbonyl in this case is presumably due to chelating effect of the aliylindium intermediate with the hydroxy function. See Paquette, L.; Lobben, P. C. J. Org. Chem., 1998, 63, 5604 and references cited therein.
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[10] For reactions of α-halocarbonyl compounds with metal in aqueous media, see: (a) Chan, T. H.; Li, C. J.; Wei, Z. Y. J. Chem. Soc., Chem. Commun. 1990, 505
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For reduction of vicinal bromohydrins by metals in aqueous media, see: Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649
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