کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5223890 | 1383501 | 2008 | 9 صفحه PDF | دانلود رایگان |
Rearrangements readily occur in Scholl oxidations and interfere with the construction of certain molecular architectures. 3,3‴,4,4′,4″,4‴,5′,5″-Octamethoxy-1,1′,2′,1″,2″,1‴-quaterphenyl and 3,3‴,4,4′,4′′,4‴,5′,5′-octamethyl-1,1′,2′,1″,2″,1‴-quaterphenyl, which were conceived as precursors to benzenoid strips, rearranged under Scholl conditions to the unexpected C2v-substituted products 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene and 1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene. This corrects a widely propagated error in the literature in which the assignments of 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene (C2v) and 1,2,5,6,8,9,12,13-octamethoxydibenzo[fg,op] naphthacene (C2h) are crossed. A mechanism involving the migration of an aryl ring on an arenium cation intermediate is proposed.
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Journal: Tetrahedron - Volume 64, Issue 50, 8 December 2008, Pages 11370–11378