Temperature Dependence of Regioselectivity in Nucleophilic Photosubstitution of 4-Nitroanisole. The Activation Energy Criterion for Regioselectivity
GG Wubbels, H Danial, D Policarpio
Index: Wubbels, Gene G.; Danial, Hanan; Policarpio, Danielle Journal of Organic Chemistry, 2010 , vol. 75, # 22 p. 7726 - 7733
Full Text: HTML
Citation Number: 5
Abstract
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 ...
Related Articles:
Microwave-assisted methylation of phenols with DMF-DMA
[Belov, Pavel; Campanella, Veronica L.; Smith, Alison W.; Priefer, Ronny Tetrahedron Letters, 2011 , vol. 52, # 21 p. 2776 - 2779]
[Maurer, Stefan; Liu, Wei; Zhang, Xiaojing; Jiang, Yongwen; Ma, Dawei Synlett, 2010 , # 6 p. 976 - 978]
Photodehalogenation of the monochloro-and monofluoroanisoles
[Siegman, John R.; Houser, John J. Journal of Organic Chemistry, 1982 , vol. 47, # 14 p. 2773 - 2779]
Daniel Vorländer. 11. 6. 1867–8. 6. 1941
[Vorlaender Chemische Berichte, 1938 , vol. 71, p. 1688,1699]
Daniel Vorländer. 11. 6. 1867–8. 6. 1941
[Vorlaender Chemische Berichte, 1938 , vol. 71, p. 1688,1699]