The ethoxyethynyl carbinol—αβ-unsaturated ester conversion: Stereomutation accompanying a selenium dioxide oxidation |
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| Authors: | MH Tankard JS Whitehurst |
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| Institution: | Department of Chemistry, the University, Exeter, EX4 4QD U.K. |
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| Abstract: | Benzsuberone reacts with ethoxyethynyl magnesium bromide to give 1-ethoxyethynyl-1-hydroxy-2,3-benzocycloheptene, which on rearrangement with mild acid (carbon dioxide) yields ethyl cis-1,2-benzo-3-cycloheptenylidene acetate (4, R′= CO2Et, R1 = H) and the corresponding trans -compound. With selenium dioxide, both esters yield the same γ-lactone, |
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