92195-63-6Relevant academic research and scientific papers
The ritter reaction under truly catalytic bronsted acid conditions
Sanz, Roberto,Martinez, Alberto,Guilarte, Veronica,Alvarez-Gutierrez, Julia M.,Rodriguez, Felix
, p. 4642 - 4645 (2007)
Simple organic acids like 2,4-dinitrobenzenesulfonic acid (DNBSA) catalyze the Ritter reaction of secondary benzylic alcohols giving rise to the corresponding N-benzylacetamides in usually high yields. Reactions can be conducted without exclusion of oxygen and without the need of dry solvents. With tertiary α,α-dimethylbenzylic alcohols a different pathway involving a formal dimerization reaction takes place under the acid-catalytic conditions used. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Formation and Reactivity of ?-Radical Cation Intermediates in the C-C Coupling Reaction of Phenyldiazomethanes by One-Electron Oxidation
Ishiguro, Katsuya,Ikeda, Masatoshi,Sawaki, Yasuhiko
, p. 3057 - 3066 (2007/10/02)
One-electron oxidation of phenyldiazomethanes afforded cis-stilbene predominantly.The reaction was independent of the oxidation methods, e.g., electrolysis, copper(II), triarylaminium salts, or photosensitized one-electron oxidtions.The C-C coupling reaction was retarded by introducing α-substituents on phenyldiazomethanes.The ESR spectra of diazoalkane radical cations could be obtained during the electrolysis at low temperature and the resulting spectra revealed their unique electronic structure as ?-radicals for most cases.When a bulky tert-butyl group was substituted, the corresponding ?-radical cation was observed, but the C-C coupling reaction did not occur.The novel HOMO-LUMO switching by one-electron removal from the HOMO ?-orbital of diazomethane is explained by the interaction of phenyl group with the C-N-N ?-radical moiety.The C-C coupling reaction proceeds via facile cycloaddition between the diazomethane and ?-radical cation, and the preferential formation of cis-olefins is based on the secondary orbital interaction between the two phenyl groups.The structure and the stability of radical cation intermediates are rationalized on the basis of ab initio calculations.
