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Upstream product

• 7512-49-4 N-phenyl-1,4-naphthoquinone monoimine 
• 90-11-9 1-Bromonaphthalene 
• 27067-30-7 naphth-1-yl phenyl nitroxide 
• 90-30-2 N-phenyl-1-naphthylamine 
• 344441-80-1 N-1-naphthyl-N-phenylhydroxylamine 
• 586-96-9 Nitrosobenzene 
• 1077-72-1 4-Diazobenzo-2,5-cyclohexadienone 

Relevant academic research and scientific papers

Ruthenium(II) Porphyrin Quinoid Carbene Complexes: Synthesis, Crystal Structure, and Reactivity toward Carbene Transfer and Hydrogen Atom Transfer Reactions

Reactivity study of novel metal carbene complexes can offer new opportunities in catalytic carbene transfer reactions as well as in other synthetic protocols. Metal complexes with quinoid carbene (QC) ligands are assumed to be key intermediates in a variety of metal-catalyzed QC transfer reactions using diazo quinones, which demands development of the chemistry of QC transfer of well characterized metal-QC complexes. Herein we report the isolation and QC transfer of ruthenium porphyrins [Ru(Por)(QC)] which contribute the first examples of (i) structurally characterized metal-QC complex (by X-ray crystallography) and (ii) isolated metal-QC complex that undergoes QC transfer reaction. The complexes [Ru(Por)(QC)] were prepared from reaction of [Ru(Por)(CO)] with diazo quinones and exhibited dual reactivity, i.e., hydrogen atom transfer (HAT) as well as QC transfer. The stoichiometric QC transfer reactions from these Ru-QC complexes to nitrosoarenes (ArNO) afforded nitrones in up to 90% yield, and the corresponding catalytic reactions were also developed. Both the stoichiometric and catalytic reactions for a series of QC ligands bearing electron-donating and -withdrawing substituents showed a reverse substituent effect on the QC transfer reactivity. Complexes [Ru(Por)(QC)] are also reactive toward C-H and X-H (X = N, S) bonds and can catalyze aerobic oxidation of 1,4-cyclohexadiene; their stoichiometric HAT reactions with unsaturated hydrocarbons gave product yields of up to 88%. The unique dual reactivity and electronic feature of [Ru(Por)(QC)] were studied by spectroscopic means and density functional theory (DFT) calculations.

Nitroxide Radicals. Part 21. Spontaneous Decomposition of N-Aryl 1- and 2-Naphthyl Nitroxides

N-Aryl 1-naphthyl nitroxides self-react in solution to give the corresponding secondary amines and N-aryl-1,4-naphthoquinone imines.When reaction at the 4-naphthyl position is hindered by substituents benzoquinone imines are also produced.N-Phenyl 2-naphthyl nitroxide under similar conditions gives the corresponding amine and 2-phenylamino-1,4-naphthoquinone via a 1,2-naphthoquinone imine N-oxide intermediate.

Reactivity and Structure of N-Phenyl-1-naphthylamines and Related Compounds. Part 3. Reaction with Oxygen-centred Radicals

Comparison is made between products obtained by oxidation of N-phenyl-1-naphthylamines and 1-naphthyl phenyl nitroxides with peroxyl radicals.It is concluded that oxidation of the amines does not proceed to a considerable extent via the nitroxides.Comparison is also made of products obtained from these amines and nitroxides by oxidation with Fremy's salt.