The title compound (3) has been obtained by rhodium(l1) catalysed decomposition and cyclization of methoxycarbonyl[2-(2'-thienyl)benzoyl]diazomethane (2) followed by spontaneous Stevens rearrangement of the initially formed sulphur ylide (1).
By comparison with six synthesized standards the identity of the following chlorinated thiophenes were established in spent kraft bleach liquors: 2,3,4-trichlorothiophene and 3-formyl and 3-acetyl di- and trichlorothiophene. The synthesized standards were found to be isomers of the thiophenes identified in the effluents. A large number of lipophilic terpene derivatives with from one to four chlorine atoms were also detected.
The synthesized chlorinated thiophenes were found to have partion coefficients (Log Pow) between 3.8 and 5.6. The compounds were found to bioaccumulate in bleak. About one third of the concentrations at the end of the exposure period remained in the fish after an elimination period of 14 days. The compounds were moderately toxic towards the harpacticoid Nitocraspinipes. Three of the compounds showed mutagenic activity.
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