23357-60-0Relevant academic research and scientific papers
Flash vacuum thermolysis of 5-(1-chloroethenyl)acenaphthene. A short synthesis of pyracylene and its bechaviour under high temperature conditions
Sarobe, Martin,Flink, Simon,Jenneskens, Leonardus W.,Zwikker, Jan W.,Wesseling, Jolanda
, p. 2125 - 2132 (2007/10/03)
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 deg C pyrolysate by recrystallization at -20 deg C.The temperature conversion data reveal that 1 decomposes and rearranges at T 1000 deg 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 cyclopentacenaphthylene (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.
