162083-76-3Relevant academic research and scientific papers
Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity
Mukherjee, Tathagata,Biswas, Soumik,Ehnbom, Andreas,Ghosh, Subrata K.,El-Zoghbi, Ibrahim,Bhuvanesh, Nattamai,Bazzi, Hassan S.,Gladysz, John A.
, p. 2486 - 2501 (2017)
The title molecules are sought in connection with various synthetic applications. The aliphatic fluorous alcohols RfnCH2OH (Rfn = CF3(CF2)n-1; n = 11, 13, 15) are converted to the triflates RfnCH2OTf (Tf2O, pyridine; 22-61%) and then to RfnCH2I (NaI, acetone; 58-69%). Subsequent reactions with NaOCl/HCl give iodine(III) dichlorides RfnCH2ICl2 (n = 11, 13; 33-81%), which slowly evolve Cl2. The ethereal fluorous alcohols CF3CF2CF2O(CF(CF3)CF2O)xCF(CF3)CH2OH (x = 2-5) are similarly converted to triflates and then to iodides, but efforts to generate the corresponding dichlorides fail. Substrates lacking a methylene group, RfnI, are also inert, but additions of TMSCl to bis(trifluoroacetates) RfnI(OCOCF3)2 appear to generate RfnICl2, which rapidly evolve Cl2. The aromatic fluorous iodides 1, 3-Rf6C6H4I, 1, 4-Rf6C6H4I, and 1, 3-Rf10C6H4I are prepared from the corresponding diiodides, copper, and RfnI (110-130 °C, 50-60%), and afford quite stable RfnC6H4ICl2 species upon reaction with NaOCl/HCl (80-89%). Iodinations of 1, 3-(Rf6)2C6H4 and 1, 3-(Rf8CH2CH2)2C6H4 (NIS or I2/H5IO6) give 1, 3, 5-(Rf6)2C6H3I and 1, 2, 4-(Rf8CH2CH2)2C6H3I (77-93%). The former, the crystal structure of which is determined, reacts with Cl2 to give a 75:25 ArICl2/ArI mixture, but partial Cl2 evolution occurs upon work-up. The latter gives the easily isolated dichloride 1, 2, 4-(Rf8CH2CH2)2C6H3ICl2 (89%). The relative thermodynamic ease of dichlorination of these and other iodine(I) compounds is probed by DFT calculations.
Mesomorphic compound, liquid crystal composition containing it, liquid crystal device using the composition, display apparatus and method
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, (2008/06/13)
An optically inactive mesomorphic compound of the formula (I) according to Claim 1 characterized by having a terminal group of: -A3-CrF2r+1, where A3 is a specific cyclic group and r is 2 - 18, is suitable as a
