Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes. |
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| Authors: | Matthew F Schlecht Ho-jin Kim |
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| Institution: | Department of Chemistry, Polytechnic Institute of New York, 333 Jay St., Brooklyn, NY 11201 USA |
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| Abstract: | Treatment of tertiary γ- and δ-hydroxyalkenes with chromium trioxide in acetic acid/acetic anhydride gives reasonable yields of γ- and δ-lactones by oxidative cyclization, with loss of one carbon. A mechanism is proposed involving formation of a chromate monoester, followed by intramolecular oxidative attack on the alkene. |
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