154110-59-5Relevant academic research and scientific papers
Mechanism of the 10-methylacridinium ion-sensitized photooxidation of N,N-dibenzylhydroxylamine and its derivatives in acetonitrile
Ohba, Yasuhiro,Kubo, Kanji,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 491 - 493 (2001)
The 10-methylacridinium ion (MA+)-sensitized photooxidation of substituted N,N-dibenzylhydroxylamines (1) in acetonitrile occurred mainly by a superoxide ion mechanism to give N-benzylidenebenzylamine N-oxides (2) and hydrogen peroxide quantitatively. Analysis of substituent effects on the limiting quantum yield for formation of 2 showed that back electron transfer (ET) from the 10-methylacridinyl radical (MA.) to the radical cation 1+. proceeds in the Marcus 'normal region'. In addition, this back ET was found to take place in preference to one-electron reduction of O2 by MA..
Imine-forming radical elimination reactions of O-(1-naphthoyl)-N,N- bis(p-substituted benzyl)hydroxylamines activated by triplet benzophenone
Andoh, Fumihiko,Kubo, Kanji,Sakurai, Tadamitsu
, p. 2537 - 2542 (2007/10/03)
It was shown that despite the occurrence of a diffusion-limited triplet energy transfer between the title hydroxylamine 1 and benzophenone, triplet 1 decomposed inefficiently giving p-substituted N-(p-substituted benzylidene)benzylamine 2 and 1-naphthoic acid (3) as unimolecular radical elimination products. The logarithm of the k(r)/k(d) ratio (where k(r) is the rate constant for homolytic cleavage of the N-O bond in triplet 1 and k(d) is that for its deactivation) used as a measure of the triplet-state reactivities of 1, showed a negligible dependence on the substituent constant. This finding was explained in terms of a very small contribution of the ionic structure to the transition state for the N-O bond homolysis.
