The clemmensen reduction of α,β-unsaturated ketones |
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Authors: | Ajoy K. Banerjee, , Jaime Alv rez G., Magaly Santana,Marí a C. Carrasco |
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Affiliation: | Ajoy K. Banerjee, *, Jaime Alvárez G., Magaly Santana,María C. Carrasco |
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Abstract: | The deoxygenation of the α,β-unsaturated ketones (1) and (5) under the Clemmensen condition yielded the olefins (2) and (6) along with their respective dimers (3+4) and (8+9). The α , β-unsaturated ketone (13) under similar treatment yielded the olefin (14) in satisfactory yield but the dimer could not be characterized. The deoxygenation of the α,β-unsaturated ketones (10) and (16) under similar con- ditions afforded the olefins (12) and (15) respectively in satisfactory yield along with the rearranged olefins (11) and (17) respectively. Epox-idation of the olefin (17) followed by heating with p-toluenesulfonic acid yielded the ketone (18). |
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