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Synthesis 1990; 1990(12): 1128-1133
DOI: 10.1055/s-1990-27112
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Preparation and Beckmann Rearrangement of O-(Chlorooxalyl)oximes

Johannes C. Jochims* , Sabine Hehl, Siegfried Herzberger
  • *Fakultät für Chemie der Universität Konstanz, Postfach 5560, D-7750 Konstanz, Germany
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Publication History

Publication Date:
02 May 2002 (online)

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Oximes 1 react with phosgene or oxalyl chloride to give O-(chloroformyl)- 2, or O-(chlorooxalyl) oximes 8, which undergo Beckmann rearrangement with antimony pentachloride to afford nitrilium hexachloroantimonates 3 in high yields. With di- or triphosgene (4 or 6) oximes 1 form mixtures of O-(chloroformyl)- 2 and O-(trichloromethoxyformyl)oximes 5. The O-(chlorooxalyl)oximes 8 further characterized as esters 10 and amides 11. With N,N-dimethylformamide the nitrilium salts 3 react to give N-acyl formamidinium salts 12.