N-alkoxy-N-acylnitrenium ions in intramolecular aromatic addition reactions was written by Glover, Stephen A.;Goosen, Andre;McCleland, Cedric W.;Schoonraad, Johan L.. And the article was included in Tetrahedron in 1987.Electric Literature of C10H13BrO This article mentions the following:
N-Alkoxy-N-acylnitrenium ions are generated by treating N-alkoxy-N-chloroamides with Ag+ ions in ethereal solvents. These intermediates readily cyclize onto aromatic nuclei on alkoxy side chains to give benzoxazines and benzoxazepines and on acyl side chains to give γ-, δ-, and ε-benzolactams. E.g., treating Ph(CH2)3ONClBz in Et2O with AgBF4 gave 50% benzoxazepine I. Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side chain aromatic rings. The yields and regioselectivities of these reactions are ascribed to different transition structures for cyclization onto the acyl and alkoxy side chains, which involve an exo- and endocyclic N+-O π-bond, resp. Evidence for this exceptionally high π-bond character is obtained from MNDO calculations, which predict a π-bond order of 0.9 and a rotational barrier of 29.7 kcal mol-1. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Electric Literature of C10H13BrO).
1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Electric Literature of C10H13BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary