Ultrasound-promoted synthesis of nitriles from aldoximes under ambient conditions

Tetrahedron Letters

Volumn 51, Issue 34, 2010, Pages 4479-4481

  Jiang, Nan ^a   Ragauskas, Arthur J ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALDOXIME; COPPER ACETATE; NITRILE; WATER;

ARTICLE; ENVIRONMENTAL TEMPERATURE; ONE POT SYNTHESIS; ULTRASOUND;

EID: 77955711324     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.079     Document Type: Article

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36. 1H NMR analysis, and then was purified by flash chromatography (n-pentane/ethyl ether = 6:1) to afford p-tolunitrile (105.1 mg, yield 90%).
37. 2.
38. 3 to replace aqueous 50 wt % hydroxylamine led to significant reduced conversion of m-tolualdoxime into m-tolunitrile (less than 30%) under identical condition.
39. 2 (9.1 mg, 0.05 mmol) was added into the vial. After capping the vial, the reaction mixture was under continuous ultrasound irradiation for another 2 h. After sonication, the reaction mixture was concentrated in vacuo, and the residue was purified by flash chromatography (n-pentane/ethyl ether = 6:1) to afford m-tolunitrile (colorless oil, 85.2 mg, yield 73%).