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Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates

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posted on 2016-12-15, 00:54 authored by Jan Wallbaum, Lennart K. B. Garve, Peter G. Jones, Daniel B. Werz
Donor–acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two acceptor groups. A variety of different donors (e.g., aryl, N, and O) are used. The stereospecificity of the reaction is demonstrated by using a chiral starting material.

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