17302-61-3Relevant articles and documents
The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study
Uliana, Marciana P.,Servilha, Bruno M.,Alexopoulos, Olga,De Oliveira, Kleber T.,Tormena, Cláudio F.,Ferreira, Marco A.B.,Brocksom, Timothy J.
, p. 6963 - 6973 (2015/11/09)
An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.
Catalytic Autoxidation of Benzoquinone Dioximes with Nitrogen Oxides: Steric Effects on the Preparation of Monomeric Dinitrosobenzenes
Rathore, R.,Kim, J. S.,Kochi, J. K.
, p. 2675 - 2684 (2007/10/02)
A convenient catalytic method for the autoxidation of quinone dioximes to dinitrosobenzenes with dioxygen is based on the presence of small amounts of nitrogen oxides.The catalytic cycle is deduced from the facile chemical oxidation of quinone dioxime to dinitrobenzene with stoichiometric amounts of the 1-electron oxidant, nitrosonium-either as the NO+BF4- salt or the disproportionated ion pair NO+NO3- derived from nitrogen dioxide.The regeneration of NO+ occurs by the subsequent oxidation of nitric oxide (NO) with dioxygen to nitrogen dioxide followed by the disproportionation to nitrosonium nitrate in the presence of electron-rich donors.Indeed, dioximes of various p-benzoquinones are shown to be strong reducing agents by transient electrochemistry.Electrochemical oxidation also leads to dinitrosobenzenes in good yields at anodic potentials of ca. 1.3 V.The substitution of p-dinitrosobenzene with bulky alkyl groups stabilizes the monomeric form, which is otherwise extensively associated.
