Single‐Step Synthesis of Biphenylene from 9‐Fluorenone in a Discharge Plasma

Abstract

the case of (6). The large increase in the ratio ( 3 ) / ( 4 ) in the series of cycloolefin derivatives (f)-(h) supports the cyclic transition state ( 5 ) . This and the strong influence of the methyl group in (b) provide evidence for the C-2 atom being situated about two bond lengths distant from the asymmetric C atom in R; such is the case only in (5). Experimental:A mixture of (2) (0.01 mole) and olefin (0.015 mole) in glacial acetic acid (20ml) was treated with a solution of conc. sulfuric acid (1.25 g) in glacial acetic acid (5 ml) (added over a period of 5 minutes). After 4 hours the reaction mixture was added with stirring t o a mixture of 8 N NaOH (100 ml) and chloroform (100 ml) at O°C. The chloroform phase was separated off, dried over potash, and the compounds (3) and ( 4 ) isolated by distillation.

Model Compound Study of the Pathways for Aromatic Hydrocarbon Formation in Soot

“…The preparation of biphenylene in a high-temperature plasma has previously been reported. [17][18][19] The NMR data, which describe the unextracted sample, increase in average size of the aromatic clusters and in the number of cross-links per cluster, were observed with increasing temperature. These data are presented in Figure 2 and Table 2.…”

“…Only in the lowest-temperature sample is biphenylene observed which can be formed from biphenyl by the loss of two hydrogens. The preparation of biphenylene in a high-temperature plasma has previously been reported. − …”

Plasma-Triggered CH4/NH3 Coupling Reaction for Direct Synthesis of Liquid Nitrogen-Containing Organic Chemicals

“…In 1967, Spedding reported the direct synthesis of hydrazine from NH 3 employing a gas discharge reactor, and he also reported the synthesis of certain unusual and highly reactive compounds, such as diboron tetrachloride (B 2 Cl 4 ), decaborane (B 10 H 16 ), oxy-fluorides (O 4 F 2 , O 2 F 2 ), and krypton and xenon tetrafluoride (KrF 4 , XeF 4 ), which are so unstable that they decompose during conventional synthesis . In 1970, Suhr reported the single-step synthesis of biphenylene from 9-fluorenone in a discharge plasma, and he also demonstrated that hydrocarbons can take place isomerization reaction, elimination reaction, bimolecular addition reaction, and selective oxidation reaction . Recently, Liu reported that long-chain hydrocarbons were produced from CH 4 plasma and CH 4 /CO 2 plasma; , Cooks published a paper reporting the selective reduction of benzene in a helium plasma; Benoit reported that nonthermal atmospheric plasma can be considered as a promising technology for enhancing the depolymerization of recalcitrant cellulose toward hydrolysis .…”