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Addition and Cyclization Reactions in the Thermal Conversion of Hydrocarbons with an Enyne Structure, 4. Formation and Rearrangements of Bicyclic C 10 H 8 Aromatics from 1‐Phenyl‐1‐buten‐3‐yne
Author(s) -
Schulz Kathrin,
Hofmann Jörg,
Zimmermann Gerhard
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971217
Subject(s) - chemistry , bicyclic molecule , naphthalene , indene , enyne , cycloisomerization , methylene , photochemistry , azulene , torr , medicinal chemistry , isomerization , radical cyclization , organic chemistry , catalysis , physics , thermodynamics
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.