FRESH ROUTES TO DERIVATIVES OF CYCLOHEPTA[DE]NAPHTHALENE

被引：14

作者：

ASHWORTH, G ^{[1
]}

BERRY, D ^{[1
]}

SMITH, DCC ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCASHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 12期

关键词：

D O I：

10.1039/p19790002995

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3-Dihydrocyclohepta[de]naphthalene-1,4-dione (1) is formed by cyclising methyl 3-(1-naphthoyl)propionate. It forms only monoacetals, gives a hemiacetal salt with alkali, and can be dehydrogenated to a quinone (14) that undergoes ring-contraction to a phenalenone (15) on acetalisation. Acenaphthylene traps dichloroketen inefficiently, allowing formation of the dirtier (19) of tetrachloroallene, but dechlorination of the acenaphthylene adduct (16) followed by opening of its cyclobutanone ring with acid gives cyclohepta[de]naphthalen- 2(1H)-one (21). This and the isomeric cyclohepta[de]naphthalen-1(2H)-one (23) obtainable from the dione (1), were reduced to alcohols with the object of preparing cyclohepta[de]naphthalene (26) by ester pyrolysis.

引用

页码：2995 / 3000

页数：6