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Digitale Medien

Butatrien durch Thermolyse von Propiolsäure-(2-propinyl)ester (1983)

Bilinski, Vanda ; Dreiding, André S. ; Hollenstein, Hans

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 66 (1983), S. 2322-2329

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Details

ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Flow thermolysis of 2-propynyl propiolate (5) at 580° afforded butatriene (6) (ca. 50%) and, as by-products, 4-methylene-2-cyclobuten-1-one (7), 2-ethynylpropenal (8), 1-penten-4-yn-3-one (9), 4-penten-2-ynal (10) (total ca. 10%), along with some propynal, acetylene, CO2 and CO. In the same way, propiolic acid (1,1-D2)-2-propynyl propiolate (11) led to (1,1-D2)-butatriene (12) and a little 4-((D2)methylene)-2-cyclobuten-1-one (13). A mechanism is proposed for the transformation of 5 into 6 and of 11 into 12, which also accounts for the formation of 7,8,9 and 10, as well as 13. The position of one of the published 13C-NMR signals of butatriene (6) must be revised. Thermolysis of methyl-(1) and ethyl propiolate (2) resulted in small yields of 2-buten-4-olide (3) and 2-penten-4-olide (4).

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19830660743

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