69967-67-5Relevant academic research and scientific papers
Radical and Nitrenoid Reactivity of 3-Halo-3-phenyldiazirines
Navrátil, Rafael,Tarábek, Ján,Linhart, Igor,Martin?, Tomá?
, p. 3734 - 3737 (2016)
3-Halo-3-phenyl-3H-diazirines (halogen = Br or Cl) undergo a dissociative single-electron transfer from alkyllithiums (RLi) in THF-based solvent mixtures. The resulting 3-phenyldiazirinyl radical, observed by EPR spectroscopy, is eventually transformed to benzonitrile. In Et2O, 2 equiv of RLi add to both nitrogens of halodiazirine N=N bond, affording N,N′-dialkylbenzamidines. The nitrenoid reactivity of some N-alkyl-1H-diazirine intermediates is manifested by their insertion into the α-C-H bond of THF or Et2O.
