title: Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO.
abstract: Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.
authors: Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400076, India.
authors: Srimanta
authors: S
authors: Manna
authors: Sandipan
authors: S
authors: Jana
authors: Tapish
authors: T
authors: Saboo
authors: Arun
authors: A
authors: Maji
authors: Debabrata
authors: D
authors: Maiti
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003653:Decarboxylation; D009573:Nitrites / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D002264:Carboxylic Acids; D003497:Cyclic N-Oxides; D009573:Nitrites; D009574:Nitro Compounds; C024225:n-butyl nitrite; C003959:TEMPO