B. Krumm, A. Vij, R. L. Kirchmeier
Jan 29, 1997
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0
Influential Citations
11
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Journal
Inorganic Chemistry
Abstract
The introduction of tetrafluoro- and pentafluorophenoxy moieties into a variety of pentafluorobenzenes C6F5R (R = CF3, CN, NO2) is accomplished by employing the trimethylsilyl ethers (siloxanes) 4-HC6F4OSiMe3 (1) and C6F5OSiMe3 (2) as transfer agents. Depending on the nature of the electrophile, the stoichiometry of the reaction, and the reaction conditions, polysubstituted polyfluorodiphenyl ethers are obtained. Excess C6F5R results in the formation of the 1,4-monosubstituted benzenes (diphenyl ethers) 4-(4‘-XC6F4O)C6F4R (R = CF3, X = H (3), F (4); R = CN, X = H (5), F (6); R = NO2, X = H (9), F (10)). When R = NO2, the 1,2-substituted isomers are also detected. Additional byproducts that are isolable are the disubstituted benzenes 2,4-(4‘-XC6F4O)2C6F3R (R = CN, X = H (7), F (8); R = NO2, X = H (11), F (12)). Excess 1 or 2, when reacted with C6F5R, results in the formation of the trisubstituted benzenes 2,4,6-(4‘-XC6F4O)3C6F2R (R = CN, X = H (13), F (14); R = NO2, = H (15), F (16)). The hydrolysis of nit...