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.
Original language | English (US) |
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Pages (from-to) | 5079-5085 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 69 |
Issue number | 25 |
DOIs | |
State | Published - Jun 24 2013 |
Externally published | Yes |
Keywords
- Azide
- EPR
- NBD
- Nitrene
- Reduction
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry