B. Boduszek, A. Halama
Oct 1, 1998
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract 4-Nitrobenzyl(α-amino)phosphonic acids treated with an excess of aqueous sodium hydroxide undergo a C-P bond cleavage and subsequent transformation into a mixture of azoxybenzene and azobenzene derivatives. The observed cleavage is an example of the intramolecular redox reaction. The phosphonate moiety is oxidized to phosphate, and the remaining part of the molecule is reduced to azoxybenzene derivative 2. After acidification of the reaction mixture two main products were isolated; 4,4′-diformylazoxybenzene (3) and 4-formyl-4′-hydroxyazobenzene (4). The product 4 was probably formed as a result of the Wallach type rearrangement of 3.