Secondary nitro group, denitration

Tritio-denitration In the presence of azoisobutyronitrile as radical initiator, tri-n-butyltin tritide can tritio-denitrate secondary and tertiary nitro compounds to give the respective labeled derivatives. Primary nitro groups can only be denitrated if they are located adjacent to keto groups . The carbanion-stabilizing properties of nitro groups facilitate the introduction of electrophiles such as alkyl halides, aldehydes and ketones at the a-position. Furthermore, nitroolefins are excellent Michael acceptors as well as dienophiles, which enables the regioselective and chemoselective synthesis of a broad range of acyclic and... 

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