title: Facile synthesis of beta-tribromomethyl and dibromomethylenated nitroalkanes via conjugate addition of bromoform to nitroalkenes.
abstract: Addition of bromoform to conjugated nitroalkenes in the presence of Mg provided beta-tribromomethyl nitroalkanes in good to excellent yields and diastereoselectivity. These novel Michael adducts, formed under radical conditions, underwent elimination of HBr in the same pot under reflux to afford beta-dibromomethylenated nitroalkanes in good yield. Alternatively, a one-pot high yielding synthesis of the dibromides was possible under anionic conditions via LDA mediated addition of bromoform to nitroalkenes.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
authors.forename: Bichismita
authors.initials: B
authors.lastname: Sahu
authors.forename: Guddeangadi N
authors.initials: GN
authors.lastname: Gururaja
authors.forename: Shaikh M
authors.initials: SM
authors.lastname: Mobin
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis*; D000475:Alkenes / Q000138:chemical synthesis*; D008274:Magnesium; D009574:Nitro Compounds / Q000138:chemical synthesis*; D022882:Trihalomethanes
chemical_list: D000473:Alkanes; D000475:Alkenes; D009574:Nitro Compounds; D022882:Trihalomethanes; D008274:Magnesium; C015044:bromoform