Crystal structure and reactivity of 2‐chloro‐3,5‐dinitrothiophene and of 2‐phenylsulphonyl‐3,5‐dinitrothiophene with nucleophiles

Abstract

AbstractThe geometry obtained by a crystal structure determination of the title compounds, as compared with that of the analogous benzene derivatives, along with results of ab initio calculations, is used to interpret the different SNAr reactivities in some thiophene and benzene compounds. The smaller rotation of the nitro groups with respect to the aromatic rings observed in thiophene derivatives should be considered a relevant factor in the higher reactivity in the thiophene series.