The behaviour of 2-nitrothiophene and of 3-nitrothiophene with some nucleophiles

The reactivity of 2-nitrothiophene (1) and of 3-nitrothiophene (II) with some nucleophiles has been studied. According to calculated electronic densities I can receive nucleophilic attack at C3 and C5 depending on the nucleophile used, but II only at C2. With N-lithium piperidine both I and II also give coupling products (VII and XI respectively) of the hithienyl type.