77133-16-5Relevant academic research and scientific papers
Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation
Lévesque, éric,Laporte, Simon T.,Charette, André B.
, p. 837 - 841 (2017/01/14)
Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.
Studies on Unstabilized ?-Sulfuranes: Synthesis of trans-1,2-Disubstituted Epoxides
Tewari, R. S.,Awasthi, A. K.,Chaturvedi, S. C.
, p. 1565 - 1568 (2007/10/02)
4-Nitrobenzylidenedimethylsulfurane, a semi-stabilized sulfonium ylide has been generated by the attack of methylsulfinyl carbanion in dimethylsulfoxide and reacted with a series of substituted benzaldehydes, furfural and benzylideneacetophenone to afford trans-1,2-disubstituted epoxides in fair to good yields.The structural assignments of the products are based on IR and NMR spectral evidences. - Keywords: 4-Nitrobenzylidenedimethylsulfurane
