期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 22, 页码 11357-11365出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo4019123
关键词
-
资金
- Research Grants Council of Hong Kong [HKUST603711, HKUST603313, CUHK7/CRF/12G]
DFT calculations have been carried out to study the Rh-catalyzed site selective ring-opening reactions of phenylcyclobutabenzenol (1a). Our calculations supported that the mechanism involves beta-carbon elimination in a rhodium(I) phenylcyclobutabenzenolato complex followed by alcoholysis. The favorable beta-carbon elimination involves the cleavage of the C(sp(2))-C(sp(3))(OH)(Ph) bond in la, which determines the site selectivity. The mechanism and regioselectivity of the related Rh-catalyzed insertion reaction of the asymmetric alkyne MeC CPh with phenylcyclobutabenzenol (1a) was also investigated. The key step involves the alkyne insertion into the Rh-C sigma bond of a species resulting from the favorable beta-carbon elimination in the rhodium(I) phenylcyclobutabenzenolato complex. The favorable insertion couples the metal-bonded carbon with the methyl-substituted carbon of MeC CPh.
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