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Cycloarenes, a New Class of Aromatic Compounds, III. - Studies towards the Synthesis of Cyclodecakisbenzene
Staab, Heinz A.,Diederich, Francois,Caplar, Vesna
, p. 2262 - 2273 (2007/10/02)
Attempts to synthesize the cycloarene 2 starting from benzophenanthrene building blocks are reported: From 3, the preparation of which along different routes is dealt with, bis(bromomethyl) and bis(mercaptomethyl) derivatives 4 and 5, respectively, were obtained.Cyclisation of 4 and 5 yielded 12 from which by sulfur extrusion the carbocyclic system 14 was prepared.Stevens rearrangement of 12 and subsequent elimination yielded 17.Scholl reaction of 14 resulted in the formation of 18 by only one-sided cyclisation.Similarly, photo-cyclodehydrogenation of 17 did not yield 2 but 19. - The new helical aromatic systems present in 18 and 19 are discussed on the basis of spectroscopic results.
