FROM PAGODANES TO DODECAHEDRANES - SEARCH FOR A SERVICEABLE ACCESS TOTHE PARENT (C20H20) HYDROCARBON

Authors
BERTAU M WAHL F WEILER A SCHEUMANN K WORTH J KELLER M PRINZBACH H
Citation
M. Bertau et al., FROM PAGODANES TO DODECAHEDRANES - SEARCH FOR A SERVICEABLE ACCESS TOTHE PARENT (C20H20) HYDROCARBON, Tetrahedron, 53(29), 1997, pp. 10029-10040
Citations number
79
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
29
Year of publication
1997
Pages
10029 - 10040
Database
ISI
SICI code
0040-4020(1997)53:29<10029:FPTD-S>2.0.ZU;2-B
Abstract
By taking advantage of the novel S(N)2 pagodane --> dodecahedrane rout es a preparatively potent access to the parent pentagonal dodecahedran e (2) was explored. The one-pot catalytic procedure (Pd/C/H-2) startin g from an eightfold functionalized secopagodane (14, C20H12Br6 (CO2 CH 3)(2)) excells in shortness but, rather erratic (33-53%), falls out of the competition. The longer route via 1,6-dicarboxyl/dibromo dodecahe dranes (35, 22) turned out as first choice with a total yield of 74-76 % based on the common pagodane precursor (13). (C) 1997 Elsevier Scien ce Ltd.