Abnormal PdII-Catalyzed Cyclization of 1-Methyl-1-(2-trimethylsilylethynyl)-2-propenyl Acetate
PdCl2(MeCN)2-catalyzed cyclization of 1-methyl-1-(2-trimethylsilylethynyl)-2-propenyl acetate (4) afforded 5-methyl-2-trimethylsilyl-1,4-cyclopentadienyl acetate (5) and 3-methyl-2-trimethylsilyl-1,3-cyclopentadienyl acetate (6) in a 1.2:1 ratio and ≥80% combined yield. The formation of 5 was antic...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1985-08-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9671 |
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| Summary: | PdCl2(MeCN)2-catalyzed cyclization of 1-methyl-1-(2-trimethylsilylethynyl)-2-propenyl acetate (4) afforded 5-methyl-2-trimethylsilyl-1,4-cyclopentadienyl acetate (5) and 3-methyl-2-trimethylsilyl-1,3-cyclopentadienyl acetate (6) in a 1.2:1 ratio and ≥80% combined yield. The formation of 5 was anticipated by analogy with previous work but that of 6 is unprecedented. Compounds 5 and 6 were trapped with N-phenylmaleimide and their fate in the absence of the trapping agent elucidated.
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| ISSN: | 0009-4293 2673-2424 |