Depolymerization of coals at low temperatures may offer advantages over thermal bond cleavage. Because bond cleavage energies of radical cations are lower than the corresponding homolytic bond cleavage energies of the same bond, generation of radical cations in coal may make possible depolymerization at lower temperatures. We seek to investigate the above possibility using single molecules containing functional groups common in coals. Since the generation of a radical cation requires the removal of an electron from a neutral molecule, a primary focus of the study will be finding oxidants that will remove an electron from compounds with structural similarity to those typically found in coals. The study will also be concerned with the decomposition of radical cations and the products formed as a result of the decomposition.

Radical cation generation in coal may make possible depolymerization at low temperature. This possibility was investigated using single molecules containing functional groups common in coals. Single- electron oxidations of 4,4{prime}-dimethoxybibenzyl (DMBB) by Fe(III) (1,10-phenanthroline){sub 3}(ClO{sub 4}){sub 3}, in refluxing CH{sub 3}CN, gave incomplete mass balances; an attempt was made to identify the additional products. Part of these products were deduced to be dimer, p-methoxybenzylated dimer of DMBB; mono, di, and tri-p- methoxybenzylated DMBB. Similar oxidations in CH{sub 2}Cl{sub 2} and sulfolane solvents gave similar results. Attempts to use other solvents were unsuccessful.