97850-58-3Relevant articles and documents
Hydrolysis of Aliphatic Bis-isonitriles in the Presence of a Polar Super Aryl-Extended Calix[4]pyrrole Container
Sun, Qingqing,Escobar, Luis,Ballester, Pablo
supporting information, p. 10359 - 10365 (2021/03/30)
We report binding studies of an octa-pyridinium super aryl-extended calix[4]pyrrole receptor with neutral difunctional aliphatic guests in water. The guests have terminal isonitrile and formamide groups, and the complexes display an inclusion binding geom
A more sustainable and highly practicable synthesis of aliphatic isocyanides
Waibel,Nickisch,M?hl,Seim,Meier
supporting information, p. 933 - 941 (2020/02/21)
Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.