13835-88-6Relevant academic research and scientific papers
Photoredox-Catalyzed C-F Bond Allylation of Perfluoroalkylarenes at the Benzylic Position
Sugihara, Naoki,Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto
supporting information, p. 9308 - 9313 (2021/06/28)
Site-selective and direct C-F bond transformation of perfluoroalkylarenes was achieved with allylic stannanes via an iridium photoredox catalyst system. The present defluoroallylation proceeds exclusively at the benzylic position through perfluoroalkyl radicals generated by a single-electron transfer from an excited photoredox catalyst to perfluoroalkylarenes. A variety of perfluoroalkyl groups are applicable: linear perfluoroalkyl-substituted arenes such as Ar-nC4F9and Ar-nC6F13and heptafluoroisopropylarenes (Ar-CF(CF3)2) underwent site-selective defluoroallylation. DFT calculation studies revealed that thein situgenerated Bu3SnF traps F-to prevent a retroreaction from the unstable perfluoroalkyl radical intermediate, and the radical intermediate favorably reacts with allylic stannanes. The synthesis of a bis(trifluoromethyl)methylene unit containing compound, which is an analog that is useful as a pharmaceutical agent for the prophylaxis or treatment of diabetes and inflammatory diseases, demonstrated the utility of this reaction.
POLYMORPHISM AND INTERMOLECULAR INTERACTIONS IN CRYSTALLINE FLUORINATED ALKYLBENZOIC ACIDS
Atakhodzhaev, A. K.,Babkov, L. M.,Zalesskaya, I. M.,Fialkov, Yu. A.,Privalko, V. P.,et al.
, p. 229 - 244 (2007/10/02)
Thermodynamic and spectral characteristics of fluorinated derivatives of alkylbenzoic acids (FABA) were studied in the temperature range 100-550 K.Experimental values of temperatures, enthalpies and entropies of phase transitions, as well as hydrogen bond energy at different temperatures and in the various physical (phase) states were compared to those for alkyl- and fluoroalkyl-benzoic acids.IR absorption spectra of substances studied were interpreted on the basis of theoretical calculations of frequencies, shapes and intensities of normal modes of molecular vibrations using the published data for related compounds.The information derived was used to construct models of packing of dimerized molecules of FABA in the crystalline state, and possible causes of the absence of mesomorphism on complete fluorination of alkyl radical were discussed.
LIQUID CRYSTALS CONTAINING FLUORINE. IX. 4-CYANOPHENYL 4-(PERFLUOROALKYL)BENZOATES AND TRANS-4-(PERFLUOROALKYL)CYCLOHEXANECARBOXYLATES
Fialkov, Yu. A.,Zalesskaya, I. M.,Yagupol'skii, L. M.
, p. 1781 - 1787 (2007/10/02)
By hydrogenation of 4-(perfluoroalkyl)benzoic esters at platinum and subsequent hydrolysis cis- and trans-4-(perfluoroalkyl)cyclohexanecarboxylic acids were obtained.A convenient method was foun for the isolation of the trans isopmers. 4-Phenyl esters of
