7419-60-5Relevant academic research and scientific papers
CLEVEAGE RATES FOR RADIOLYSIS-PRODUCED RADICAL ANIONS OF NAPHTHYLMETHYL PHENYL ETHERS AND NAPHTHYL BENZYL ETHERS
Guthrie, Robert D.,Patwardhan, Manjiri,Chateauneuf, John E.
, p. 147 - 152 (2007/10/02)
Cleveage reactions of α- and β-naphthylmethyl phenyl ethers and of α- and β-naphthyl benzyl ethers were studied by pulse radiolysis.Transient spectra indicate that reactions occur via electron capture followed by cleavage of the resultant radical anions to give arylmethyl radicals and aryloxide ions.Product studies of extensively irradiated samples are consistent with this scheme and show patterns which are informative for radiation studies in general.The reactions were studied in several solvents.The behavior of transient spectra obtained in acetonitrile for these ethers shows clearly that radical anions of the naphthylmethyl ethers cleave more rapidly than do the radical anions of the naphthyl benzyl ethers.
1-Naphthylcarbene: Spectroscopy, Kinetics, and Mechanisms
Barcus, R. L.,Hadel, L. M.,Johnston, L. J.,Platz, M. S.,Savino, T. G.,Scaiano, J. C.
, p. 3928 - 3937 (2007/10/02)
The reactions of 1-naphthylcarbene have been examined by using laser flash photolysis techniques.Generation of the carbene from the diazo precursor in hydrocarbon solvents leads to the formation of 1-naphthylmethyl radicals, which were characterized by their absorption at 363 nm.However, product studies in cyclohexane and cyclohexane-d12 reveal that the main reaction path is carbene insertion into the C-H bond rather than H abstraction. 1-Naphthylcarbene reacts readily with nitriles to yield nitrile ylides which can also be generated from the corresponding azirine.For example, the carbene reacts with acetonitrile with a rate constant of 4.6 X 1E5 M-1s-1 at 300 K to yield an ylide that can be trapped readily with electron-deficient olefins, such as diethyl fumarate.Reaction of the carbene with oxygen (k = 3.5 X 1E9 M-1 s-1) yields the carbonyl oxide (λmax 435 nm).Other reactions examined include halogen abstraction, addition to ketones, and reactions with triethylamine, pyridine, and ethers.The absolute kinetics of the various reactions were examined by monitoring the formation of the products (e.g., ylides, radicals, etc.), since the carbene spectrum was not detected directly.
