Carbon-oxygen bond-cleavage reactions by electron transfer. 4. Electrochemical and alkali-metal reductions of phenoxynaphthalenes

TA Thornton, GA Ross, D Patil, K Mukaida…

Index: Thornton, Todd A.; Ross, Gerald A.; Patil, Dilip; Mukaida, Kenichi; Warwick, Jeffrey O.; et al. Journal of the American Chemical Society, 1989 , vol. 111, # 7 p. 2434 - 2440

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Citation Number: 15

Abstract

Abstract: The reductions of I-(1) and 2-phenoxynaphthalene (2) to their respective radical anions were observed at-2.42 and-2.18 V vs SCE. Cyclic voltammetric and chronoamperometric studies indicate that both radical anions have half-lives that are greater than 100 s in dry N, N-dimethylformamide. Controlled-potential electrolysis of the ethers resulted in relatively slow, regioselective carbon-oxygen bond cleavage to produce ...