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 | Zendy

Schulz Kathrin | Zendy; Hofmann Jörg | Zendy; Zimmermann Gerhard | Zendy

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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.

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