Intramolecular anodic carbon-carbon bond-forming reactions of oxidized phenol intermediates leading to spirodienones. Structural effects on reactivity and evidence …

JS Swenton, K Carpenter, Y Chen…

Index: Swenton, John S.; Carpenter, Kenneth; Chen, Ying; Kerns, Michael L.; Morrow, Gary W. Journal of Organic Chemistry, 1993 , vol. 58, # 12 p. 3308 - 3316

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Citation Number: 61

Abstract

Anodic oxidation of 4-phenylphenol in methanol leads to 4-methoxy-4-phenylcyclohexa-2, 5dienones whereas anodic oxidation of 4-(2-alkenylphenyl)-phenols leads to spirocyclic 2, 5- cyclohexadienones in competition with methanol addition to the 4-position. Using 4- phenylphenol and 442-propenylpheny1) phenol as model systems, the optimum conditions for solvent addition versus carboncarbon bond formation have been studied. The yield of ...