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- W1969965601 abstract "N-alkoxy-N-acylnitronium ions are generated by treatment of N-alkoxy-N-cohloroamides with silver ions in ethereal solvents. These intermediates readily cyclise onto aromatic nuclei on alkozy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ϵ benzolactams. Spirane products are formed by ipso addition When a 4-methoxy substituent ia present on the side-chain aromatic rings. The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyolic and endocyclic N-0 π-bond. Evidence for this exeptionally high π-bond character has been obtained from MNDO calculations which predict a π-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1" @default.
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- W1969965601 date "1987-01-01" @default.
- W1969965601 modified "2023-10-12" @default.
- W1969965601 title "N-alkoxy-n-acylnitrenium ions in intramolecular aromatic addition reactions" @default.
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- W1969965601 doi "https://doi.org/10.1016/s0040-4020(01)81665-3" @default.
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