The Pagodane Route to Dodecahedranes: Chemistry and Structure of Bissecododecahedranes

✍ Scribed by Dipl.-Chem. Georg Lutz; Dr. Dieter Hunkler; Prof. Dr. Horst Prinzbach; Grety Rihs

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: English
• Weight: 407 KB
• Volume: 28
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198902981

✦ Synopsis

The energy-rich C2,H2, hydrocarbon I1 .l.l.l]pagodane A (X = Y = H)"] can be converted into dodecahedrane B (X = Y = Z = H) catalytically[21 as well as stepwise (via C, D and E).['] The yields of these procedures, yet encouraging in view of the ready availability of the starting materials, remain unsatisfactory for several reasons:['] persistence of intermediates (e.g. 7 ; cf. 13, 14)J4] "hyper~tabiIity",[~.~l particularly at the mono-ene step D, and the conditions necessary for the final dehydrogenative C-C bond formation E +. B.13,61 Limits drawn by this step E+ B regarding a variable substitution of the pagodane and (seco)dodecahedrane frameworks[41 are the subject of this communication.

Several promising ways out of this dilemma by functionalization of the four methylene positions (X, Y) are conceivable, and will be outlined in the two directly following communications.~7~g1