Facile synthesis of beta-tribromomethyl and dibromomethylenated nitroalkanes via conjugate addition of bromoform to nitroalkenes.
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.
Sahu
Bichismita
B
Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
Gururaja
Guddeangadi N
GN
Mobin
Shaikh M
SM
Namboothiri
Irishi N N
IN
D000473:Alkanes / Q000138:chemical synthesis*; D000475:Alkenes / Q000138:chemical synthesis*; D008274:Magnesium; D009574:Nitro Compounds / Q000138:chemical synthesis*; D022882:Trihalomethanes
D000473:Alkanes; D000475:Alkenes; D009574:Nitro Compounds; D022882:Trihalomethanes; D008274:Magnesium; C015044:bromoform