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[Display omitted] 1-Alkylsulfanyl-4-X-2,3,5,6-tetrafluorobenzenes (X = CF 3 , H; alkyl = Me, Bn, CHF 2) upon reactions with nitromethane in the presence of DBU undergo replacement of 2 or 3-positioned fluorine atoms by a nitromethyl group to afford the corresponding (nitromethyl)trifluoroarenes. The calculations of the transition states using the DFT method correctly predict the ratios of reaction products. In the cases of relative sulfones, only 2-positioned fluorine atom undergoes substitution; however, the sulfonyl group can also be displaced by a nitromethyl moiety. [ABSTRACT FROM AUTHOR]