Electrophilic Substitutions on (1, 1, 2, 3, 3, 3-Hexafluoropropyl)-oxy- and -thio-benzene

Abstract

The nitration and bromination of (1, 1, 2, 3, 3, 3-hexafluoropropyl)-oxy-(2) and -thio-benzene (3) were investigated. ln the nitration of (2), the para substitution was more predominant over theorthosubstitution comparing with those of the non- orinated alkoxybeRzenes. The nitration and bromination of (3) proceeded without diflliculty to give mono-substituted products.These results wereascribed to the inductive effect of the electron attractive -ZCF2CHFCF, (Z=O and S) groups. From the 9F NMR data of m and P-fluoro-(2).and (3), the 6, and oR values were determined for-ZCF2CHFCFs groups (Table 2) The most favorable condition for the preparation of (2) and (3) were also studied.