1433738-28-3Relevant academic research and scientific papers
An unexpected copper catalyzed 'reduction' of an arylazide to amine through the formation of a nitrene intermediate
Peng, Hanjing,Dornevil, Kednerlin H.,Draganov, Alexander B.,Chen, Weixuan,Dai, Chaofeng,Nelson, William H.,Liu, Aimin,Wang, Binghe
, p. 5079 - 5085 (2013)
Azido nitrobenzoxadiazole (NBD) was observed to undergo a 'reduction' reaction in the absence of an obvious reducing agent, leading to amine formation. In the presence of an excess amount of DMSO, a sulfoxide conjugate was also formed. The ratio of these two products was both temperature- and solvent-dependent, with the addition of water significantly enhancing the ratio of the 'reduction' product. Two intermediates of the azido-NBD reaction in DMSO were trapped and characterized by low-temperature EPR spectroscopy. One was an organic free radical (S=1/2) and another was a triplet nitrene (S=1) species. A mechanism was proposed based on the characterized free radical and triplet intermediates.
