From pagodanes to dodecahedranes - Search for a serviceable access to the parent (C20H20) hydrocarbon

被引：45

作者：

Bertau, M ^{[1
]}

Wahl, F ^{[1
]}

Weiler, A ^{[1
]}

Scheumann, K ^{[1
]}

Worth, J ^{[1
]}

Keller, M ^{[1
]}

Prinzbach, H ^{[1
]}

机构：

[1] UNIV FREIBURG,CHEM LAB,INST ORGAN CHEM & BIOCHEM,D-79104 FREIBURG,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(97)00345-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By taking advantage of the novel S(N)2 pagodane --> dodecahedrane routes a preparatively potent access to the parent pentagonal dodecahedrane (2) was explored. The one-pot catalytic procedure (Pd/C/H-2) starting from an eightfold functionalized secopagodane (14, C20H12Br6 (CO2 CH3)(2)) excells in shortness but, rather erratic (33-53%), falls out of the competition. The longer route via 1,6-dicarboxyl/dibromo dodecahedranes (35, 22) turned out as first choice with a total yield of 74-76% based on the common pagodane precursor (13). (C) 1997 Elsevier Science Ltd.

引用

页码：10029 / 10040

页数：12

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