Tetrahedron

Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes

T Inokuchi, H Kawafuchi

Index: Inokuchi, Tsutomu; Kawafuchi, Hiroyuki Tetrahedron, 2004 , vol. 60, # 51 p. 11969 - 11975

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Citation Number: 26

Abstract

Sodium 2, 2, 6, 6-tetramethylpiperidine-N-oxide (TEMPO− Na+), generated by reduction of TEMPO· with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion.