| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5218239 | Tetrahedron | 2013 | 7 Pages |
Abstract
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hanjing Peng, Kednerlin H. Dornevil, Alexander B. Draganov, Weixuan Chen, Chaofeng Dai, William H. Nelson, Aimin Liu, Binghe Wang,