1983
DOI: 10.1055/s-1983-30499
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A Mild, High-Yield Conversion of Aldoximes into Nitriles using Trichloroacetyl Chloride/Triethylamine

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Cited by 31 publications
(3 citation statements)
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“…The cyano-substituted A1 azoalkane was obtained from the corresponding oxime 2a through dehydration with trichloromethyl chloroformate 16 in acetonitrile. The isonitrile-and acetylene-functionalized azoalkanes A′2 and A′3 were synthesized by Horner-Emmons olefination of the azoaldehyde A with the respective known phosphonates in THF.…”
Section: Resultsmentioning
confidence: 99%
“…The cyano-substituted A1 azoalkane was obtained from the corresponding oxime 2a through dehydration with trichloromethyl chloroformate 16 in acetonitrile. The isonitrile-and acetylene-functionalized azoalkanes A′2 and A′3 were synthesized by Horner-Emmons olefination of the azoaldehyde A with the respective known phosphonates in THF.…”
Section: Resultsmentioning
confidence: 99%
“…Tolunitriles are traditionally synthesized from the dehydration of amide [6] or aldoxime [7], cyanation of aryl chloride [8,9] or of toluic acid [10,11] and diazotization of toluidine [12], etc. However, these methods usually require expensive starting materials or lead to serious pollution and are not suitable for industrial production on a large scale.…”
Section: Introductionmentioning
confidence: 99%
“…3 The conversion of aldehydes into the corresponding nitriles is an important organic transformation. This procedure is usually achieved by dehydration of the corresponding aldoximes using classical reagents 4 or new milder ones such as phosphorus diiodide, 5 trichloro-acetyl chloride, 6 chlorosulfonyl isocyanate, 7 or chlorosulfonyl fluoride. 8 Bejoy Thomas 9 has reported conversion of aldehydes oxime into nitriles using solid acid as catalysts, but it needs high temperature and long reaction time.…”
Section: Introductionmentioning
confidence: 99%