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NMR investigations on boron complexes in the conjugate addition on alpha,beta-unsaturated imides
G Cardillo1, L Gentilucci, M Gianotti
1Dipartimento di Chimica G. Ciamician and CSFM-CNR, Università di Bologna, via Selmi 2, 40126 Bologna, Italy. cardillo@ciam.unibo.it
Organic Letters
|May 12, 2001
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.