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Corner Opening of Cyclopropane by Mercury(II) and Thallium(III) and Transmetallation of the Intermediate Organomercurials: A  Novel, Stereoselective Approach to Cyclobutanes and Cyclopropanes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
1994 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 116, no 1, 186-197 p.Article in journal (Refereed) Published
Abstract [en]

The reactivity of the two isoelectronic cations (Hg2+ and T P ) toward the cyclopropane ring is compared, and further evidence for the exclusive corner selectivity for Hg2+ is provided by isotope labeling. Cleavage of cyclopropyl derivative 1 with Hg(NO3)2, followed by KBr quenching, afforded the stable, rearranged organomercurial 3,  whose transmetalation has been studied. Whereas reaction of 3 with Pd(I1) afforded lactol 4,  treatment with MezCuLi resulted in the formation of cyclobutanol derivative (3 - 29);  analogous conjugate addition has also been accomplished (32 - 35). Similarly, the organomercurial 22, obtained from 21  as the major product on the Hg(I1)-mediated ringopening, reacted with MezCuLi or AlC13 to give the ring-closure product 21. These reactions representa novel method for the stereoselective construction of four- and three-membered rings. The stereochemistry of the key steps of these transformations has been established by using stereospecifically deuterated substrates lb, 3b, 21b, and 22b.

Place, publisher, year, edition, pages
1994. Vol. 116, no 1, 186-197 p.
National Category
Natural Sciences
URN: urn:nbn:se:uu:diva-140708DOI: 10.1021/ja00080a021OAI: oai:DiVA.org:uu-140708DiVA: diva2:384247
Available from: 2011-01-08 Created: 2011-01-08 Last updated: 2012-01-26Bibliographically approved

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