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Periodic Acid, a Novel Oxidant of Polycyclic, Aromatic Hydrocarbons

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Periodic Acid, a Novel Oxidant of Polycyclic, Aromatic Hydrocarbons JOURNAL OF RESEARCH of the National Bureau of Standards - A. Physics and Chemistry Vol. 72A, No.4, July- August 1968 Periodic Acid, a Novel Oxidant of Polycyclic, Aromatic Hydrocarbons * Alexander J. Fatiadi Institute for Materials Research, National Bureau of Standards, Washington, D.C. 20234 (April 1, 1968) Certain polycycli c, aromatic hydrocarbons can be oxidized with periodic acid in aprotic solvents co ntaining a small proportion of water. A unique, two·fold character of response to pe riodic acid by these hydrocarbons has been found: (1) producti on of a coupling reaction through a radical in ter­ mediate [conve rsion of pyre ne into l,l'-b ipyrene, and fluore ne into 1,2-b is(2,2'-bipheny lylene)ethyle neJ or (2) conversion into qui nones by a two-equivalent ox idation mechanis m that does not involve a radical int ermediate [acenaphthene, anthracene, a nthrone , benz[alanthracene, naphthacene, naphthalene, and phenanthrene]. Little or no reacti on was observed whe n oxidation was attempted wi th sodium meta­ periodate in stead of pe riodi c acid . Electron-s pin resonance revealed no radical intermediate in th e ox id ati on of malonic ac id with either periodic acid or sodium periodate. Key Words: Aproti c solvents; aromatic hydrocarbons; malonic acid ; periodic acid; pyrene radical; quinones; reacti on mecha ni s m; sodium metape ri odate. 1. Introduction oxidation on solids [1], on e-electron transfer oxidation [26], and various other methods [27]. Recentl y in this laboratory [1] , I the fate of certain P eriodi c acid (o r its salts) has been used extensively of the polycyclic, aromatic hydrocarbons that have for cleavage of 1,2-glycols, and a-hydroxy-aldehydes been identified as cons tituents of polluted air has been and -ketones [28- 33]. In aprotic solvents containing studied under conditions simulating those that these some water, periodic acid has been used for the oxi­ substances encounter as air pollutants; that is, (a) in dative hydroxylation of an active methylene group the presence of ultraviolet irradiation, (b) exposure to [34- 36] , for oxidative cleavage of enols and reductones air and s li ght heat, and (c) contact with powdered [37, 38] , and for hydroxylation and further oxidation solids (particulates). Oxidation of many of the hydro­ of compounds containing an isolated double bond, carbons studied occurs under such conditions. In e.g., cinnamic acid [39] and cholesterol [40] . order ·to identify the products, it was necessary to The application of periodic acid alone as an oxidant synthesize possible oxidation products for use as for polycyclic, aromatic hydrocarbons has not hitherto reference materials. been reported [33, 41]. Sodium metaperiodate has, The main object of the present report is to describe however, been used conjointly with s uch diol-forming the usefulness of periodic acid for the oxidation of agents as osmium tetraoxide or ruthe nium tetraoxide pol ycyclic, aromatic hydrocarbons. Numerous reagents [42]. The present study s hows that, wh e n it reacts with certain polycyclic, aromatic compounds, periodic 1 have been used to effect such oxidations, including the Milas reagent [2], the Fenton reagent [3] , benzoyl acid has the ability to (1) produce radi cals by abstrac­ peroxide [4, .5 ] , benzyl radicals [6] , ph enyl radicals tion of (a) electrons or (b) protons, (2) oxidize a methine [7] , and oth er free-radical reagents [8] , lead tetra­ group at an activated double bond of polycyclic, acetate [9, 10] , ozone [11- 14] , and peroxy acids [I.5 ] aromatic compounds, or (3) oxidize an activated I in cludi ng hydrogen peroxide in acetic acid [16] , methylene group. i peroxyaceti c acid [17, 18] , and peroxytriAu oroacetic 'T acid [19- 21]. In addition, there are autooxidations 2. Reaction Conditions [22] , metabolic oxidation [23] , peroxidase oxidation [24] , photooxidation using solutions [2.5], photo- 2.1 . Solvent *Prel illlinary co mmunic ation: Che rn . CO llllllun. 1967, to87. The choice of a solvent in which to oxidize polycyclic, l Fi gures in urac kets indicate the lit erature refe re nces allhe e nd of this paper. aromatic hydrocarbons with periodic acid appears to 341 be very important. In the present work, glacial acetic compound having the phe ne structure and one active acid was usually the first so lvent investi gated ; some­ methine group [pyre ne (I)], and (3) compounds having times, propionic acid could be used. In most cases, one or two active methylene groups [anthrone (8 ), oxidations in formi c acid afford lower yie ld s than in acenaphthe ne (15), and flu orene (20)]. Maloni c acid acetic acid. A seri es of aproti c solv e nts, mi scible with (14), which has an acti ve methylene group, was also water and relatively stable in th e presence of periodic ox idized. In addition, the following co ndensed-rin g, acid at elevated temperature, was tri ed. These solvents, polycyclic, aromatic hydrocarbons we re tested: in th e order of their decreasing sta bility to the oxidant biphe nyl , c hrysene, coronene, Au oranthe ne, perylene, are: N,N-dimethylformamide, p-dioxane, acetonitrile, picene, p-terphenyl, and triphenylene. acetone, tetrahydrofuran, methyl s ulfoxide, and acetic anhydride. Methyl s ulfoxid e was used in the oxidation of anthracene with good results, but its application 3. Results and Discussion with other hydrocarbons has not ye t been f'xplored. The stability of N,N-dimethylformamide in the pres­ 3.1. Effect of Solvent ence of periodic acid has previously bee n indicated [43] . Such solvents as formamide, 2-methoxyethanol, bis(2·methoxyethyl) ether (di glyme), or 1,2-dimethoxy­ The effect of various solv ents on the reacti on may ethane are not suitable as the reaction medium, be­ be seen from the following examples: ox idation of cause of in stability in the presence of periodic acid' phenanthrene (1 0 ) with periodic acid gave a poor at elevated te mperature. When aceti c 'anhydride -.va", yie ld (3-6%) of phenanthre nequinone (II) in N ,N· used .in the oxidation of pyrene with pe riodic acid, dimethylformamide or in glacial acetic acid, but a with application of heat, a violent reaction occurred. good yield (45- 55%) in p-dioxane. Anthracene (5 ) affurded a moderate yield (30%) of anthraquinone (6 ) in acetic acid, a good yield (50 to 60%) in acetone or .2.2. Temperature methyl sulfoxide, and an excellent yield (90%) in To initiate oxidation of polycyclic, aromatic hydro­ N,N-dimethylformamide. Naphthalene (7 ) in p-dioxane carbons with periodic acid, some degree of heating was practi cally unaffected; but, in aceti c acid, showed was found to be necessary. In the conversion of pyrene oxidation in good yield (70%) to '1,4-naphthoquinone (I ) into 1.l'-bipyrene (2) only mild warming (40 to (9 ). Naphthacene (3 ) gave a low yield (10- 15%) of 50 °C) was necessary; however, dimerization of flu orene naphthacenequinone (4 ) when oxidized in p -dioxane (20) into 1,2-bis(2,2'-biphe nylylene)ethylene (24) re­ or aceti c acid, but an exce ll ent yield (80%) in N,N­ quired a much hi gher te mperature. The oxidations dimeth ylfo rmamide . Pyrene (I ) was not oxidized in that resulted in quinone formation us ually require 5 N,N-dimethylformamide, p-dioxane, acetone, or to 10 min of heating at 95 to 130 °C to start; then the e thanol, but was oxidized in acetic acid. Fluore ne te mperature must be lowered to 60 to 80 °C to avoid (20) was not affected in N,N-dimethylformamide, vi gorous and some times violent reaction. Usually, the p·dioxane, or acetonitrile, but dimerized in acetic acid. beginning of the oxidation (and the end of the induc· It may be concluded from these experime nts that the tion period) is noted by a change of the reaction solvent participates in th e overall reaction process. medium from colorless to red or brown-red; sometimes, As noted by Ritchie and co-workers [44] , the effect this is followed by evolution of iodine vapor. of the solvent on reactions in solution is associated with a so-called solve nt reorganizati on, and this factor may make an appreciable contribution to energies of 2.3. Proportion of the Oxidant activation in solution. Furthe rmore, the polarity of the solvent may partake in promotion of the rate Oxidative d im erization of pyrene (I ) to 1,l'·bipyrene of oxidation, by hydrogen bonding in the transition (2 ) was effected with a 1 : 1 mole ratio of periodic acid state. to hydrocarbon. In this reaction, it was possihle to de monstrate stoic hiometric consumption of the per­ iodic acid. However, in the oxidation of the other hvdro­ 3.2. General Reactivity of Polycyclic, Aromatic carbons to quinones, approximately 4.2 moles of the Compounds Toward Periodic Acid oxidant were used per mole of hydrocarbon. This proportion was emplo yed on the assumption that, in Results obtained in this study on the acti on of each hydrocarbon molecule, two methine or me thylene periodic acid on a variety of polycyclic, aro matic groups become hydroxylated and then oxidized to the hydrocarbons reveal that linear and angular poly­ corresponding quinone. cyclic, aromatic hydrocarbons having the acene structure (anthracene, benz[a]anthracene, naph­ 2.4. Compounds Oxidized thacene, pentaceue, and their analogs) [45] are the most reactive; next are the condensed·ring aromatic Three kinds of polycyclic, aromatic hydrocarbons compounds having the phene structure (acenaphthe ne, were used in the oxidati ons: (1) compounds having benzo[a]pyrene, pyrene, etc.) [46] ; and c hrysene and the acene structure with two active methine groups picene are less reactive.
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