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Chemoselective Lactam Formation in the Addition of Benzenesulfonyl Bromide to N-Allyl Acrylamides and N-Allyl 3,3-Dimethylacrylamides

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journal contribution
posted on 12.03.1999, 00:00 by Chen Wang, Glen A. Russell
Chemoselectivity in the addition and cyclization reactions of PhSO2Br to N-allyl acrylamides has been confirmed due to the higher reactivity of the acrylic CC bond toward the sulfonyl radical than that of the allyl CC bond. Formation of γ-lactams by Cβ→Cα cyclization can be achieved with N-allyl 3,3-dimethylacrylamides.