期刊
CANADIAN JOURNAL OF CHEMISTRY
卷 87, 期 1, 页码 307-313出版社
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
DOI: 10.1139/V08-145
关键词
Brook silene; alkyne; cycloaddition; reaction mechanism; mechanistic probe
资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- University of Western Ontario
- Ontario Photonics Consortium
The addition of the alkyne-containing mechanistic probes (trans-2-phenylcyclopropyl)ethyne, (trans, trans-2-methoxy-3-phenylcyclopropyl)ethyne, and (trans, trans-2-methoxy-1-methyl-3-phenylcyclopropyl)ethyne (1a-1c) to a Brook silene 2-(1-adamantyl)-2-trimethylsiloxy-1,1-bis(trimethylsilyl)-1-silene (14) was examined. When alkyne 1a was added to the silene, an ene adduct was observed; however, addition of alkyne 1c to 14 gave a mixture of silacyclobutenes and silacycloheptenes. The regiochemistry of the phenyl and methoxy substituents on the seven-membered ring of the silacycloheptenes provides convincing evidence for the formation of a biradical intermediate along the reaction pathway.
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