Vn. Boiko et al., THE ACTIVATION OF S(N)AR REACTIONS BY THE SUPERSTRONG ELECTRON-WITHDRAWING SUBSTITUENT CF3S(O)=NSO2CF3, Journal of fluorine chemistry, 67(2), 1994, pp. 119-123
The chlorine lability of the 2-nitrochlorobenzene derivative which con
tains the superstrong electron-withdrawing substituent CF3S(O)=NSO2CF3
in position 4 has been compared with the analogous 4-trifluoromethyls
ulphonyl derivative and picryl chloride in nucleophilic substitution.
During interaction with hard nucleophilic agents, the effect of one su
perstrong substituent approximately corresponds to the influence of tw
o nitro groups in positions 2 and 4. With soft reagents, picryl chlori
de is more active than the compound containing the CF3S(O)=NSO2CF3 gro
up, polarizable only with difficulty.