Formation of cyclopent[hi]acephenanthrylene from 1,2-, 1,3-, 1,4- and 2,3-triphenylenedicarboxylic acid derivatives on flash vacuum pyrolysis at >900 degrees C

被引：10

作者：

Banciu, MD ^{[1
]}

Brown, RFC ^{[1
]}

Coulston, KJ ^{[1
]}

Eastwood, FW ^{[1
]}

Jurss, C ^{[1
]}

Mavropoulos, I ^{[1
]}

Stanescu, M ^{[1
]}

Wiersum, UE ^{[1
]}

机构：

[1] AKZO CORP,NL-6800 SB ARNHEM,NETHERLANDS

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1996年 / 49卷 / 09期

关键词：

D O I：

10.1071/CH9960965

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The processes involved in the conversion of triphenylene, C18H12, into cyclopent [hi]acephenanthrylene, C18H10, under flash vacuum pyrolytic conditions at 900-1100 degrees C have been investigated by pyrolysing triphenylene-1,2- and -2,3-dicarboxylic anhydrides and diallyl triphenylene-1,3- and -1,4-dicarboxylates to give the corresponding didehydrotriphenylenes in the gas phase. These didehydro intermediates are converted into mixtures of cyclopent[hi]acephenanthrylene and triphenylene in different yields and proportions. Pyrolysis of 9,10-diethynylphenanthrene; C18H10, yields cyclopent[hi] acephenanthrylene in good yield. Pyrolysis of 1-nitrotriphenylene and allyl triphenylene-2-carboxylate to give the triphenplen-1-yl and -2-yl radicals leads to formation of the same products. Mechanisms involving radical rearrangements (C18H11 species) and benzyne-cyclopentadienylidenecarbene and ethyne-ethenylidene rearrangements (C18H10 species) are discussed.

引用

页码：965 / 976

页数：12

共 29 条

[1] FLASH VACUUM PYROLYSIS OF PHENANTHRENE-3,4-DICARBOXYLIC ANHYDRIDE AND OF CYCLOBUTA[C]-PHENANTHRENE-1,2-DIONE - PRODUCTS OF RING CONTRACTION, INSERTION AND RING CLEAVAGE [J].