Nitrobenzyl (α-amino)phosphonates. Part 2[1]. Cleavage of 4-nitrobenzyl(α-amino)phosphonic acids in aqueous sodium hydroxide solution

Article abstract of DOI:10.1080/10426509808033736

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.

Full text of DOI:10.1080/10426509808033736

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NITROBENZYL(α-
AMINO)PHOSPHONATES.
PART 2[1]. CLEAVAGE
OF 4-NITROBENZYL(α-
AMINO)PHOSPHONIC ACIDS IN
AQUEOUS SODIUM HYDROXIDE
SOLUTION
Bogdan Boduszek a & Agnieszka Halama a
a Institute of Organic Chemistry, Biochemistry and
Biotechnology Wrocław University of Technology ,
50-370, Wrocław, Poland
Published online: 24 Sep 2006.
To cite this article: Bogdan Boduszek & Agnieszka Halama (1998) NITROBENZYL(α-
AMINO)PHOSPHONATES. PART 2[1]. CLEAVAGE OF 4-NITROBENZYL(α-
AMINO)PHOSPHONIC ACIDS IN AQUEOUS SODIUM HYDROXIDE SOLUTION,
Phosphorus, Sulfur, and Silicon and the Related Elements, 141:1, 239-250, DOI:
10.1080/10426509808033736
To link to this article: http://dx.doi.org/10.1080/10426509808033736
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