AI Article Synopsis
- The reaction involves 2,2,2-trichloroethyl alkyl ethers treated with 2 equivalents of CuCl and bpy in refluxing DCE, resulting in the selective formation of (Z)-1-alkoxy-2-chloroethenes.
- This process occurs through a 1,2-H shift in a copper-chlorocarbenoid intermediate.
- Similarly, 2,2,2-trichloroethyl carboxylates react via a radical 1,2-acyloxy shift under the same conditions.
Article Abstract
Reaction of 2,2,2-trichloroethyl alkyl ethers with 2 molar equiv of CuCl/bpy in refluxing DCE yielded (Z)-1-alkoxy-2-chloroethenes stereoselectively as the major product via 1,2-H shift in copper-chlorocarbenoid intermediate. 2,2,2-Trichloroethyl carboxylates undergo a radical 1,2-acyloxy shift under similar conditions.
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| http://dx.doi.org/10.1021/ol8006524 | DOI Listing |
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