Fluorene derivatives Hydroxylation

Oxidation of some fluorene derivatives, such as 1-hydrofluorene or fluorene-1-carboxylic acid, does not produce polymer films. Two explanations have been proposed [186]. First, strong electron withdrawing groups such as carboxylic acid may destablize the fluorene radical cation and promote reactions with the solvent or anions. Conversely, donor substituents such as hydroxyl groups may stabilize the fluorene cation radical intermediates enough so that the radicals may diffuse away... 

The first, unequivocal evidence for N-hydroxylation of an aromatic amine in vivo was obtained with 2-(acetamido)fluorene, which was detected in urine as its N-hydroxy derivative almost entirely in the form of a D-glucuronic acid conjugate (that could be cleaved by /3-d-glucosiduronase), to which structure 133 was assigned.362,383 Activation of chemical carcinogens (that are not themselves reactive, but are... 

Tertiary amines are transformed into A-oxides (generally less toxic), but primary and secondary amines are oxidized into hydroxylated derivatives (hydroxylamines). This oxidation is responsible for the hepatotoxicity and mutagenicity of acetamino-2-fluorene (Figure 33.11). ... 

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