ORGN 438 |
| We report here the progress toward the synthesis of full wheel–shaped hexagonal pi–system 1 consisting of six dehydrobenzo[12]annulene ([12]DBA) units, which represents a substructure of ultimate two–dimensional carbon network, graphyne. On the basis of our synthesis of trefoil–shaped tris[12]DBA through single bond formation by intramolecular pinacol coupling followed by double elimination to form triple bonds, we planned to synthesize 1 using the same synthetic method. Thus in situ deprotection–cross coupling reaction of TMS–protected hexaethynylbenzene 2 and diformyliodobenze derivative 3 gave hexasubstituted benzene 4 in 70% yield. Pinacol coupling of dodecaaldehyde 4 using a low–valent vanadium reagent gave dodecaol 5 in 13% yield. Further elaboration toward the synthesis of 1 will be presented.
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Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
