Anodic oxidation of 1,3-di(paratolyl)-5-paratoluidinomethyl-1,3,5-diazaphosphorinane on aluminum

2014 
1102 Aminomethylphosphines pertain to one of the rare types of easily available hybrid polyfunctional phosphine ligands. Aminomethylphosphine based systems are used as specific ligands in coordination chemistry for creating water soluble [1–3], chiral [4–6], polynuclear compounds and clusters [7–9] and also biomimetic catalysts of several electrochem ical processes [10–13]. The results of studies of elec trochemical properties of aminomethylphosphines, for the most part, cyclic diazaphosphorinanes, is described in [14–17]. The anodic behavior of para toluidinomethyl 1,3,5 diazaphosphorinane I (DP) was studied most thoroughly. As was shown earlier, the result of electrochemical oxidation of I depends on the anode material. Thus, when glassy carbon was used, the reaction products contained salts of diazaphos phorinanium II and spirotetraazaphosphonium III [14]. At the same time, the oxidation on platinum pro duced bicyclic dimer IV in place of product III [15]. On the other hand, the anodic oxidation of DP on mercury led to the formation of a complex with a new P, N ligand V [18]. In line with the possible forma tion of new types of metallocomplexes, it seemed interesting to study the oxidation of DP on a soluble anode such as aluminum, which is a р element, in contrast to mercury (d element). The results of this experiment are shown in this publication.
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