One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst

Akbar Heydari; Morteza Mehrdad; Hossein Tavakol

doi:10.1055/s-2003-41454

SHORTPAPER

One-Pot Synthesis of α-Substituted Hydroxylamine Derivatives from Aldehydes Using Lithium Perchlorate/Diethyl Ether as a Catalyst

Akbar Heydari*^a, Morteza Mehrdad^b, Hossein Tavakol^a
^a Chemistry Department, Tarbiat Modarres University, P. O. Box 14155-4838, Tehran, Iran
Fax: +98(21)8006544; e-Mail: akbar.heydari@gmx.de;
^b Department of Phytochemistry, Shahid Beheshti University, Evin 1983963113, Tehran, Iran

Abstract

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Abstract

O-(Trimethylsilyl)oxime ethers, generated in situ by reaction of aldehydes and O-(trimethylsilyl)hydroxylamine in lithium perchlorate/diethyl ether solution, are highly reactive species and undergo facile reaction with silylated nucleophiles, such as trimethylsilyl cyanide and the binary reagent (MeO)₃P/Me₃SiCl, to give α-substituted hydroxylamine derivatives.

Key words

lithium perchlorate - oximes - α-substituted hydroxylamines

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