Factors in Molecular Structure to Activate Nitro Compounds for Organic Transformations

Activation of nitro compounds was accomplished by introduction of angle strain, γ,δ-unsaturation, or a γ-silyl group. Results from a systematic study indicate that coexistence of two or more of these factors in aliphatic nitro compounds allowed transformations to take place under ambient conditions upon catalysis with AlCl3, TiCl4, BF3·OEt2, or SnCl4. Consequently, structurally modified nitro starting materials led to products in the class of nitroalkyl cyclopentadiene, cyclohydroxamic ester, and chlorohydroxamic acid.