Alkoxycarbonyl- and Carboxylate-Group Migrations in the Benzilic Acid Rearrangement of Ethyl Cyclopropane-2, 3-dioxopropionate |
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| Authors: | Hans Dahn Lê H Dao Rannoo Hunma |
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| Abstract: | In alkaline medium C3H5? CO? C (OH)2? COOEt ( 1b ) is transformed into C3H5? C (OH)(COOH)2 ( 2a ). Labelling experiments show that the cyclopropyl group is not shifted, but only ROOC and/or ?O2C groups. GC./MS. and NMR. analysis after incomplete reaction show that both ROOC- and ?O2C-groups Migrate; at higher pH (ca. 14) the ester group rearrangement seems to be more important than at pH ca.9-10. |
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