title: NMR investigations on boron complexes in the conjugate addition on alpha,beta-unsaturated imides.
abstract: [reaction: see text]. The 1,4-addition of O-benzylhydroxylamine to alpha,beta-unsaturated imide 1 in the presence of BF3.Et2O proceeds with the preferential attack of the nucleophile on the Cbeta-re face. To explain this unexpected reactivity 1H, 13C, and 11B NMR investigations have been carried out on the boron-imide complex, which show the presence of an S-cis imide chain conformation.
authors.affiliation: Dipartimento di Chimica G. Ciamician and CSFM-CNR, Università di Bologna, via Selmi 2, 40126 Bologna, Italy. cardillo@ciam.unibo.it
authors.forename: G
authors.initials: G
authors.lastname: Cardillo
authors.forename: L
authors.initials: L
authors.lastname: Gentilucci
authors.forename: M
authors.initials: M
authors.lastname: Gianotti
authors.forename: A
authors.initials: A
authors.lastname: Tolomelli
mesh_terms: D000535:Aluminum / Q000737:chemistry; D001895:Boron / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry; D006898:Hydroxylamines / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical
chemical_list: D002614:Chelating Agents; D006898:Hydroxylamines; D007094:Imides; C017064:benzyloxyamine; D000535:Aluminum; D001895:Boron