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

Liebigs Annales

Volumn , Issue 12, 1997, Pages 2535-2539

  Schulz, Kathrin ^a   Hofmann, Jörg ^a   Zimmermann, Gerhard ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Cyclization; Pyrolysis, gas phase; Rearrangement

Indexed keywords

EID: 0344574383     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719971217     Document Type: Article

References (18)

1. J. Hofmann, G. Zimmermann, K.-H. Homann, Liebigs Ann. 1995, 841-848.
2. L. T. Scott, M. M. Hashemi, D. T. Meyer, H. W. Warren, J. Am. Chem. Soc. 1991 113, 7082-7084.
3. G. Zimmermann, U. Nüchter, S. Hagen, M. Nüchter, Tetrahedron Lett. 1994, 35, 4747-4750.
4. P. W. Rabideou, A. H. Abdourazak, H. E. Folsom, Z. Marzinow, A. Sygula, R. Sygula, J. Am. Chem. Soc. 1994, 116, 7891-7892.
5. R. F. C. Brown, F. W. Eastwood, K. J. Harrington, G. L. McMullen, Aust. J. Chem. 1974, 27, 2393-2402.
6. H. Hopf, H. Berger, G. Zimmermann, U. Nüchter, P. G. Jones, I. Dix, Angew. Chem. 1997, 109, 1236-1238;
7. Angew. Chem. Int. Ed. Engl. 1997, 34, 1187-1190.
8. J. Becker, C. Wentrup, E. Katz, K.-P. Zeller, J. Am. Chem. Soc. 1980, 102, 5110-5112.
9. U. Nüchter, G. Zimmermann, V. Franke, H. Hopf, Liebigs Ann. 1997, 1505-1515.
10. G. Zimmermann, M. Nüchter, M. Remmler, M. Findeisen, H. Hopf, L. Ernst, C. Mlynek, Chem. Ber. 1994, 127, 1747-1753.
11. Under the conditions of our experiments, trans-1 is, of course, partly converted into cis-1. At 550°C the trans/cis ratio was determind to be about 2.7. Above 600°C, the ratio amounts to about 1.8, it is independent of the kind of diluent gas used in each case.
12. S. W. Benson, Int. J. Chem. Kinet. 1989, 21, 233-243;
13. S. W. Benson, Int. J. Chem. Kinet. 1992, 24, 217-237.
14. J.A. Kerr, M. J. Parsonage, Evaluated Kinetic Data on the Gas Phase Addition Reaction: Reactions of Atoms and Radicals with Alkenes, Alkynes, and Aromatic Compounds, Butterworth, London, 1976.
15. J. Hofmann, K. Schulz, A. Altmann, M. Findeisen, G. Zimmermann, Liebigs Ann. 1997, 2541-2548.
16. H. G. Struppe, J. Ahlheim, U. Luther, B. Ondruschka, Chem. Technik 1995, 47, 179-189.
17. R. Giesa, R. C. Schulz, Makromol. Chem. 1990, 191, 857-863.
18. C. Courtot, Ann. Chim. 1915, 4, 58-62.