Non-pentagonal unsaturated dodecahedranes - In-plane delocalized 4C/3e radical cations and σ-bishomoaromatic 4C/2e dications

Tetrahedron Letters

Volumn 41, Issue 24, 2000, Pages 4763-4767

  Weiler, Andreas ^a   Quennet, Edith ^a   Keller, Manfred ^a   Exner, Kai ^a   Prinzbach, Horst ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

CV oxidation; Homododecahedranes; In plane delocalization; Unsaturation; bishomoaromaticity

Indexed keywords

ALKENE DERIVATIVE; AROMATIC COMPOUND; DODECAHEDRANE DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; OXIDATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0012625384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00721-8     Document Type: Article

References (25)

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8. © Martin, H.-D.; Mayer, B.; Weber, J.; Prinzbach, H. Liebigs Ann. 1995, 2019.
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14. Sharma, V.; Keller, M.; Weiler, A.; Hunkler, D.; Prinzbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2858. The cyclization step 11→12 (Scheme 1) is patterned after the general strategy A→B.
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17. 16,21]docos-2(20)-ene), even more oxygen-sensitive than 7, was prepared under careful exclusion of air by standard reduction (Li/tert-BuOH,/THF) of dibromo-ene B (R=H, Nu=Br).
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21. Crystallographic data for 7 have been deposited with the Cambridge Crystallographic Data Centre, Cambridge, UK. Copies of the data can be obtained free of charge (e-mail: deposit@chemcrys.cam.ac.uk) on quoting the deposition number CCDC 405336.
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23. Nevertheless, with 6 available in g-quantities, the transformation of the diamines 8 via the respective diols into 11,17-dione C is being pursued. The latter and derivatives are attractive inter alia for the study of defined multiple-path through-bond interactions.
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25. cp=1.69 V measured for a structurally related face-to-face diene-anhydride: Grimme, W.; Geich, H.; Lex, J.; Heinze, J. J. Chem. Soc., Perkin Trans. 2 1997, 1955.