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Paper | Regular issue | Vol 41, No. 3, 1995, pp.431-438
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6870
Reactions of 8H-Furo[3,4-d]dibenz[b,f]azepine and 9H-Tribenz[b,d,f,]azepine with t-Butyl Hypochlorite and Silver Trifluoroacetate. Attempts to Form a Long-lived Aromatic Nitrenium Ion

Holly C. Axtell, Kathleen B. McHugh, and Michael C. Cann*

*Department of Chemistry, University of Scranton, Scranton, PA 18510-4626, U.S.A.

Abstract

Attempts to prepare aromatic and thus potentially long-lived nitrenium ions from 8H-furo[3,4-d]dibenz[b,f]azepine (19) and 9H-tribenz[b,d,f]azepine (34) were unsuccessful. Reaction of 19 with t-butyl hypochlorite results in chlorination of the furan ring (25), while reaction of 19 with silver trifluoroacetate forms a mixture of the cis- and trans-dimethoxydihydrofurans (32) and (33). Reaction of 34 with t-butyl hypochlorite leads to a mixture of mono-, di- and trichloroazepines (37-42). The reaction of silver trifluoroacetate with 34 yields silver metal and unreacted 34.