Oxidation of Dibenzo[a,e]fluoranthene by Osmium Tetroxide

Abstract

Dibenzo[a,e]fluoranthene is treated by osmium tetroxide, the nature, structure, and configuration of the compound obtained (a trans dihydro diol) are defined taking into account the chemical, theoretical, and physicochemical arguments.

Chemical carcinogenesis. 93. Synthesis of potential phenolic metabolites of benzo[b]fluoranthene

“…c A 4.6 mm X 250 mm Vydac 201 TP104 10-gm column eluted from 70% CH3OH in H20 to 100% CHgOH in 90 min at 1 mL/min. 9-Hydroxy-BbF ( 9) was synthesized by treatment of 10,11,11 with Pd/C. The syntheses of 10-hydroxy-BbF (10) and 11-hydroxy-BbF (11) are outlined in Scheme III.…”

“…9-Hydroxy-BbF ( 9) was synthesized by treatment of 10,11,11 with Pd/C. The syntheses of 10-hydroxy-BbF (10) and 11-hydroxy-BbF (11) are outlined in Scheme III. These were accomplished by employing the base-catalyzed condensation procedure for preparation of BbF derivatives.12 Since fluorene was the starting material, no isomeric mixtures were produced as in the synthesis of 5.…”

“…These were accomplished by employing the base-catalyzed condensation procedure for preparation of BbF derivatives.12 Since fluorene was the starting material, no isomeric mixtures were produced as in the synthesis of 5. Preparation of 12-hydroxy-BbF (12) was accomplished by treatment of 10,11, with Pd/C, as in the syntheses of 1 and 9. Phenolic metabolites of PAH can be identified by their characteristic UV spectra and by their chromatographic retention times. Figure 2 illustrates the UV spectra of 1_12 13 The HPLC and capillary GC retention times of compounds 1-12 are summarized in Table I.…”

“…10-Hydroxy-BbF (10). A solution of BBrs (0.25 g, 1 mmol) in CH2C12 was added via a syringe to a stirred solution of 44 (0.28 g, 1 mmol) in CH2C12 at 0 °C under N2.…”

A study of chemical carcinogenesis. 84. Synthesis and fluorescence spectra of structural analogs of potential benzo[b]fluoranthene-DNA adducts

“…The configuration of the double bond in 6 is not known. 2-Vinylfluoranthene (9) was synthesized from 2-(bromomethyl)fluoranthene by treatment with hexamethylenetetramine to give fluoranthene-2-carboxaldehyde (20), followed by Wittig reaction with methyltriphenylphosphonium bromide. 3-Vinylfluoranthene (10) was prepared by reduction of 3-(carboxymethyl) fluoranthene with LiAlH4 to 3-(2-hydroxyethyl)fluoranthene ( 21), reaction with SOCl2, and dehydrohalogenation.…”