FeCl2-Catalyzed Intramolecular Chloroamination Reactions

Holger Danielec; Jan Klügge; Björn Schlummer; Thorsten Bach

doi:10.1055/s-2005-918500

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Synthesis 2006(3): 551-556
DOI: 10.1055/s-2005-918500

PSP

FeCl₂-Catalyzed Intramolecular Chloroamination Reactions

Holger Danielec, Jan Klügge, Björn Schlummer, Thorsten Bach*
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315; e-Mail: thorsten.bach@ch.tum.de;

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Publication History

Received 5 October 2005
Publication Date:
21 December 2005 (online)

Abstract
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Abstract

2-Alkenyloxycarbonyl azides 1 and 2-alkynyloxycarbonyl azides 3 undergo in the presence of trimethylsilyl chloride and catalytic amounts of FeCl₂ an intramolecular chloroamination (aminochlorination) reaction (Procedure 1). The corresponding oxazolidinones 2 and 4 are formed in moderate to excellent yields (47-99%). The same reagent combination can be employed to convert azides 6 of γ,δ-unsaturated carboxylic acids into the corresponding lactams 7. The latter reaction is best conducted as a one-pot reaction (Procedure 2) starting from the acids 5 without isolation of the corresponding azides (57-75% yield).

Key words

aminations - chloroaminations - chlorolactamizations - homogenous catalysis - iron - radical reactions

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1

Present address: Degussa (China) Co., Ltd., 55 Chundong Road, Xinzhuang Industry Park, Shanghai 201108, P.R. China.

2

Present address: LANXESS Fine Chemicals, LXS-FCH-RD-LP2, Geb. Q18, R 304, 51369 Leverkusen, Germany.