title: Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO.
abstract: Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective nitration of a broad range of olefins. This work discloses a new and efficient approach wherein starting from olefin, nitroalkane radical formation and subsequent transformations lead to the desired nitroolefin in a stereoselective manner.
authors: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
authors: Soham
authors: S
authors: Maity
authors: Srimanta
authors: S
authors: Manna
authors: Sujoy
authors: S
authors: Rana
authors: Togati
authors: T
authors: Naveen
authors: Arijit
authors: A
authors: Mallick
authors: Debabrata
authors: D
authors: Maiti
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000737:chemistry*; D015394:Molecular Structure; D009573:Nitrites / Q000737:chemistry*; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003497:Cyclic N-Oxides; D009573:Nitrites; D009574:Nitro Compounds; D012834:Silver; C003959:TEMPO