Temperature Dependence of Regioselectivity in Nucleophilic Photosubstitution of 4-Nitroanisole. The Activation Energy Criterion for Regioselectivity

GG Wubbels, H Danial, D Policarpio

文献索引：Wubbels, Gene G.; Danial, Hanan; Policarpio, Danielle Journal of Organic Chemistry, 2010 , vol. 75, # 22 p. 7726 - 7733

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被引用次数: 5

摘要

Photosubstitution of the nitro group vs the methoxy group of triplet 4-nitroanisole by hydroxide ion in water leads to product yields of about 80% 4-methoxyphenol and 20% 4- nitrophenol. The ratio depends slightly on temperature from 3 to 73° C. The slight temperature variation in the yield ratio is reproduced almost perfectly with a simple Arrhenius model for a mechanism involving bonding of hydroxide ion with the triplet state ...