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1,2-Di(9-anthryl)ethane (1,2-DAE) was used as a model for coal to study the C -C bond cleavage of the ethano linkage in the radiolysis of solutions containing NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2  [NaAlH 2 (OR) 2 ]. Transient species were investigated by pulse radiolysis of solutions of 1,2-DAE in THF, DME and toluene in the absence and the presence of NaAlH 2 (OR) 2 . In the presence of NaAlH 2 (OR) 2  stabilized, long-lived radical anion/sodium cation pairs of 1,2-DAE were generated even in the non-polar solvent toluene. The reaction mechanisms differ substantially for solutions in the ether solvents (THF or DME) and for solutions in toluene. Steady-state radiolysis ( 60 Co γ-rays) of solutions of 1,2-DAE in toluene containing NaAlH 2 (OR) 2  resulted in the C -C bond cleavage of the ethano linkage. This is attributed to the unstable dianion (1,2-DAE 2- , 2Na + ) formed in two successive radiation- induced reductions via (1,2-DAE ∙-  , Na + ). The resulting (9-anthryl)methyl carbanionic fragments C 14 H 9 CH 2  - , Na +  react with AlH(OR) 2  generated in the process, to form the aluminate salts [C 14 H 9 CH 2 AlH(OR) 2  - , Na + ]. From the aluminate salts, 9-methylanthracene (9- MA) was obtained by hydrolysis in yields up to 65 wt.%.

zeitschrift für naturforschung b

Radiation-Induced C -C Bond Cleavage in 1,2-Diarylethanes as Model Compounds of Coal, Part 3. Pulse and Steady-State Radiolysis of 1,2-Di(9-anthryl)ethane in Organic Solvents