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2-Metallated Oxazoles; pKa Dependent Deuterations, NMR Studies and Palladium Catalysed Coupling

2-Metallated Oxazoles; pKa Dependent Deuterations, NMR Studies and Palladium Catalysed Coupling,10.1016/0040-4020(95)00498-W,Tetrahedron,Eleanor Crowe

2-Metallated Oxazoles; pKa Dependent Deuterations, NMR Studies and Palladium Catalysed Coupling   (Citations: 8)
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Deuteration experiments on 2-lithiated oxazoles show a pKa dependent regioselectivity suggesting that the ring cleaved tautomer dominates the equilibrium. Transmetallation to the zinc derivative gives a species which behaves as a C2 ring closed nucleophile as judged by deuteration and palladium catalysed coupling experiments. These conclusions are supported by nmr spectroscopy studies of the metallated species.
Journal: Tetrahedron , vol. 51, no. 32, pp. 8889-8900, 1995
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