Abstract: | Syntheses of benzo3,4]phenanthro1,2-b]thiophene, benzo3,4]phenanthro2,1-b]thiophene and their 1-methyl analogs are reported as potential constituents of solvent refined coal liquids and for mutagenicity testing. The attempted synthesis of the 13-methyl analogs which gave the 11-methyl isomers is also described. Total assignments of the 1H- and 13C-nmr spectra based on long range optimized heteronuclear protoncarbon two-dimensional chemical shift correlation are reported. Carbon assignments obtained for benzo3,4]-phenanthro1,2-b]thiophene using this approach were confirmed with a 125 MHz 13C–13C INADEQUATE spectrum. X-Ray crystal structures were determined for benzo3,4]phenanthro1,2-b]thiophene and 1-methyl-benzo3,4]phenanthro2,1-b]thiophene. Both molecules were helically distorted from planarity. Close intramolecular contacts between the bay region H1–H13 and ClMe-H13 of 2.03 and 2.28 Å, respectively, were responsible for the distortions. There were no close intermolecular contacts of <3.5Å. both molecules refined to an R value of <0.05. |