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8687746 
Journal Article 
Anodic Decarboxylation of Glycidic Acids 
Waters, JA; Witkop, B 
1971 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
36 
21 
3232-3235 
English 
Electrolytic oxidation of sodium glycidates 4, 5, and 6 in methanol at a platinum electrode gave α,β-unsaturated ketones 7, 9, and 11 and α-methoxy ketones 8, 10, and 12, respectively. Steroidal glycidate 14, derived from 5α-cholestan-3-one, gave 3-acetyl-5α-cholest-2-ene (15) and 3ξ-acetyl-3ξ-methoxy-5α-cholestane (16) in 32 and 11% yields, respectively. Anodic oxidation of the aromatic glycidate 17 gave a low yield of neutral material consisting of numerous compounds. The mechanism of the decarboxylation and epoxide ring opening is discussed. 1971, American Chemical Society. All rights reserved.