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

[摘要] 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. (C) 2004 Elsevier Ltd. All rights reserved.

[发布日期] 2004-12-13

[关键词] TEMPO and compounds;oxidation;reduction;mCPBA;DIBAL-H;aldehyde