Thianthrene chemical reactivity

The radical 198 parallels its thianthrene equivalent 178 in exhibiting an interesting chemical reactivity which has been explored by Shine s group. In general, the radical is susceptible to attack at S by nucleophiles (cf. 180-182 for comparable products from 178). 

In addition, there is evidence that a class of compounds including thianthrene(II), phenoxathiin(VIIb) and phenoxazine(Vb) may be present in this coal. These compounds are thermally quite reactive and would probably not survive extended pyrolysis or liquefaction conditions. Instead, they will convert into the more stable dibenzothiophenes. This would suggest that chemical or biological removal of these compounds could be more efficient than a thermal process. Work is in progress to better characterize these structures by among other approaches HRMS/MS. 

---