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DOI: 10.1055/s-0030-1260211
A Novel Method for Preparing Isocyanides from N-Substituted Formamides with Chlorophosphate Compounds
Publikationsverlauf
Publikationsdatum:
07. September 2011 (online)
Abstract
Treatment of N-substituted formamides with chlorophosphate compounds such as PhOPOCl2, EtOPOCl2, Me2NPOCl2, and (PhO)2POCl and tertiary amines such as triethylamine, pyridine, and N,N-diisopropylethylamine produced the corresponding isocyanides in high yields. This method can be used to prepare various alkyl and aryl isocyanides.
Key words
isocyanide - isonitrile - formamide - dehydration - dichlorophosphate - monochlorophosphate
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References
Chemicals whose acute toxicity by the oral absorption is 50 mg/kg or less are defined as specific controlled poisonous substances under the Poisonous and Deleterious Substances Control Law by National Institute of Health Sciences in Japan. Acute toxicities of POCl3, EtOPOCl2, and PhOPOCl2 are the following according to MSDS of Tokyo Chemical Industry Co., Ltd. and Wako Pure Chemical Industries, Ltd.; POCl3 36 mg/kg (orl-rat), EtOPOCl2 220 mg/kg (orl-rat), PhOPOCl2 850 mg/kg (orl-mam).