A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond?
Chemical Communications Pub Date: 2019-08-12 DOI: 10.1039/C9CC05694G
Abstract
A new type of zwitterionic nitrosoalkene generated in situ from dehydrohalogenation of α-halo-N-alkylhydroxamic acids was designed. [4+2] cycloadditions of this heterodiene to olefins provide a facile route to construct six-membered heterocycles containing an N–O bond and a new protocol for 1,2-syn carbohydroxylate alkenes with a hydroxyl and acetamide group. DFT calculations support a concerted cycloaddition pathway and the solvent HFIP can stabilize the transition state through H-bonding interaction.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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