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January 1, 1996Journal of the Chemical Society Perkin Transactions 2

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

Martin Sarobe Simon Flink Leonardus W. Jenneskens Jan W. Zwikker Jolanda Wesseling

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Abstract

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 °C pyrolysate by recrystallization at –20 °C. The temperature conversion data reveal that 1 decomposes and rearranges at T⩽ 1000 °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 Cl4H8 potential energy surface.

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Sarobe et al. (1996) studied this question.

synapsesocial.com/papers/6a83619ae01485c92eeefbc3 https://doi.org/10.1039/p29960002125

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