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Addition and Cyclization Reactions in the Thermal Conversion of Hydrocarbons with an Enyne Structure, 4. Formation and Rearrangements of Bicyclic C10H8 Aromatics from 1-Phenyl-1-buten-3-yne

✍ Scribed by Schulz, Kathrin ;Hofmann, Jörg ;Zimmermann, Gerhard

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
524 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The thermal conversion of 1‐phenyl‐1‐buten‐3‐yne (1) into the cycloisomerization products naphthalene (2), azulene (3), and 1‐methylene‐1__H__‐indene (4) has been studied at temperatures between 550 and 1000°C, a reaction time of approximately 0.3 s at 13 Torr (FVP) and at low partial pressures in a quartz flow system. The results obtained by FVP as well as in the presence of chemically modified diluent gases suggest a predominance of unimolecular cycloisomerizations to 2 and 3 which are, however, always accompanied by radical cyclization reactions to 2 and 4 even under FVP conditions if temperatures above 550°C are applied.

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## Abstract The 4‐substituted 1‐phenyl‐1‐butene‐3‐ynes 1a–c and the 2‐ethynylstyrenes 7a–c were subjected to high‐temperature pyrolysis. The cycloisomerization products isolated suggest that these are formed by three competing processes: by (i) an electrocyclic or a molecule‐induced, (ii) an alkeny