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2005
Pyridine derivatives
R 0380
Reactivity of TEMPO Anion as a Nucleophile and Its Applications for Selective
of Haloalkanes or Acyl Halides to Aldehydes. — O-Alkylated
14- 148 Transformations
and O-acylated TEMPO derivatives (III), (VIII), and (XI) are prepared by treatment of
alkyl or acyl halides with the TEMPO anion. Oxidation of products (III) or (V) by
MCPBA affords the corresponding aldehydes and ketones. Reduction of O-acyl products (XI) by excess of iBu2AlH gives selectively aldehydes. Over-reduction to carbinols
is negligibly small owing to the chelating ability of the Tmp group for stabilization of
the hydride-adduct intermediate. — (INOKUCHI*, T.; KAWAFUCHI, H.;
Tetrahedron 60 (2004) 51, 11969-11975; Dep. Biosci. Biotechnol., Fac. Eng.,
Okayama Univ., Okayama 700, Japan; Eng.) — Klein
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