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DOI: 10.1055/s-2005-918500
FeCl2-Catalyzed Intramolecular Chloroamination Reactions
Publication History
Publication Date:
21 December 2005 (online)

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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References
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2Present address: LANXESS Fine Chemicals, LXS-FCH-RD-LP2, Geb. Q18, R 304, 51369 Leverkusen, Germany.