Flash vacuum thermolysis of 5-(1-chloroethenyl)acenaphthene. A short synthesis of pyracylene and its behaviour under high temperature conditions

被引：29

作者：

Sarobe, M ^{[1
]}

Flink, S ^{[1
]}

Jenneskens, LW ^{[1
]}

Zwikker, JW ^{[1
]}

Wesseling, J ^{[1
]}

机构：

[1] UNIV UTRECHT,DEBYE INST,DEPT PHYS ORGAN CHEM,NL-3584 CH UTRECHT,NETHERLANDS

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1996年 / 10期

关键词：

D O I：

10.1039/p29960002125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flash vacuum thermolysis (FVT) of 5-(1-chloroethenyl)acenaphthene (4) has been found to give rise to pyracylene (1). Pure 1 can be isolated from the 1100 degrees C pyrolysate by recrystallization at -20 degrees C. The temperature conversion data reveal that 1 decomposes and rearranges at T greater than or equal to 1000 degrees C; acenaphthylene (11), 1-ethynyl- (23) and 3-ethynyl-acenaphthylene (24) have been identified. The formation of 23 and 24 indicates that 1 rearranges to the transient cyclopent[bc]acenaphthylene (20) via a single ring-contraction-ring-expansion mechanism under FVT conditions. The experimental data are supported by semiempirical AM1 calculations of the C14H8 potential energy surface.

引用

页码：2125 / 2131

页数：7

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