期刊
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
卷 91, 期 6, 页码 465-471出版社
CANADIAN SCIENCE PUBLISHING, NRC RESEARCH PRESS
DOI: 10.1139/cjc-2012-0159
关键词
(phenylethynyl)sulfone; radical addition; sulfonyl-substituted norpinanes; tricyclo[4.1.0.0(2,7)]heptane; cyclization
Methyl-, phenyl-, p-chlorophenyl-, and p-tolyl(phenylethynyl)sulfones under photochemical or thermal initiation add to the central bicyclobutane C1-C7 bond of 1-R(H, Me, Ph)-tricyclo[4.1.0.0(2,7)]heptanes anti-selectively, and form norpinic adducts containing a phenylethynyl group in a geminal to substituent R position, and an endo-oriented sulfonyl group in position 7. The corresponding ketones were prepared by the hydration of the anti-adducts by the method of Kucherov. The ketone with a methylsulfonyl substituent under reflux in toluene in the presence of KOH powder and the phase-transfer catalyst (TEBA-Cl) afforded the tricyclic sulfone.
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