期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 21, 页码 8290-8297出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo901919m
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资金
- National Science Foundation [CHE-0450722, 0749759]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0749759] Funding Source: National Science Foundation
2-Triethoxysilyi-substituted 1,3-butadiene has been prepared in 30-g quantities from chloroprene via a simple synthetic procedure. Silatrane- and catechol-substituted analogues of this main group element substituted diene were then prepared on a 10-g scale by ligand exchange and characterized by X-ray crystallography in addition to standard spectroscopic techniques. 2-Dimethylphenylsilyl-1,3-butadiene has also been prepared from chloroprene on an 8-g scale. Diels-Alder reactions of these dienes are reported as well as subsequent TBAF-assisted/Pd-catalyzed Hiyama cross-coupling reactions of those Diels-Alder adducts Silicon-substituted cycloadducts and cross-coupled products were also characterized by NMR spectroscopy and, in two cases, by X-ray crystallography.
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