Synthesis and aldol cyclotrimerization of 4,7-di-tert-butylacenaphthenone

被引：7

作者：

Amick, Aaron W. ^{[1
]}

Griswold, Keith S. ^{[1
]}

Scott, Lawrence T. ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2006年 / 84卷 / 10期

关键词：

aromatic; decacyclene; hydrocarbon; nonalternant; polycyclic;

D O I：

10.1139/V06-062

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient grain scale synthesis of the previously unknown 4,7-di-tert-butylacenaphthenone (3b) is reported. The facile isomerization of epoxide 9b to ketone 3b occurs simply on stirring a solution of 9b with silica gel at room temperature. Aldol cyclotrimerization of 3b with titanium tetrachloride gives 2,5,8,11 14 1 7-hexa-tert-butyldecacyclene (1b) in 58% isolated yield. X-ray crystal structures have been obtained for the synthetic intermediates 4,7-di-tertbutylacenaphthene (2b) and 4,7-di-tert-butylacenaphthylene (8b).

引用

页码：1268 / 1272

页数：5

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