Butatrien durch Thermolyse von Propiolsäure‐(2‐propinyl)ester
作者： Vanda Bilinski , André S. Dreiding , Hans Hollenstein
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摘要: 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 (11) led to (1,1-D2)-butatriene (12) a little 4-((D2)methylene)-2-cyclobuten-1-one (13). A mechanism is proposed for transformation 5 into 6 11 12, which also accounts formation 7,8,9 10, well 13. The position one published 13C-NMR signals must be revised. Thermolysis methyl-(1) ethyl (2) resulted in small yields 2-buten-4-olide (3) 2-penten-4-olide (4).
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