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Digitale Medien

Naphthalene Isotopomers from Isotope-Labelled Phenyl-Annelated 1,3-Hexadien-5-ynes Facilitate an Evaluation of Competing Radical Cycloisomerization Pathways (1998)

Schulz, Kathrin ; Hofmann, Jörg ; Findeisen, Matthias ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2135-2142

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ISSN: 1434-193X

Schlagwort(e): Pyrolysis ; 1,3-Hexadien-5-ynes ; Cyclization, radical ; 13C, D labelling ; Naphthalene isotopomers ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The thermal cycloisomerization of the isotope-labelled 1-phenyl-1-buten-3-ynes 1 {including the [3-13C,4-D]1-phenyl-1-buten-3-yne (6) and the [4-D]1-phenyl-1-buten-3-yne (9) formed as intermediates} has been studied. The investigations were performed in a quartz flow system at a temperature of 650 °C (1, 6) [and over the range 625-750 °C for (9)] at a reaction time of 0.3 s in the presence of different diluent gases (H2, N2, N2-toluene). Spectroscopic analyses of the naphthalene isotopomers formed allow the evaluation of competing radical reaction channels in addition to reactions occuring by electrocyclic and carbene-like ring closure.[1] A mechanistic analysis for the conversion of 1 undoubtedly suggests a predominant reaction course via phenyl-type radical intermediates (1c/6c), followed by their exocyclization to the indenylcarbenyl radicals 1f/6f and the homoallyl-like rearrangement of the latter to the 1,2-dihydronaphthyl radicals 1i/6i at 650 °C. With increasing temperature, other competing reactions (endocyclizations of vinyl- and phenyl-type radicals as well as neophyl-like rearrangements of the indenylcarbinyl radicals 1f/6f) gain in importance.

Materialart: Digitale Medien

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