92424-06-1Relevant articles and documents
Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry
Umemoto, Teruo,Garrick, Lloyd M.,Saito, Norimichi
supporting information; experimental part, p. 461 - 471 (2012/07/01)
Various arylsulfur pentafluorides, ArSF5, have long been desired in both academic and industrial areas, and ArSF5 compounds have attracted considerable interest in many areas such as medicines, agrochemicals, and other new materials, since the highly stable SF5 group is considered a "super-trifluoromethyl group" due to its significantly higher electronegativity and lipophilicity. This article describes the first practical method for the production of various arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides), from the corresponding diaryl disulfides or aryl thiols. The method consists of two steps: (Step 1) treatment of a diaryl disulfide or an aryl thiol with chlorine in the presence of an alkali metal fluoride, and (step 2) treatment of the resulting arylsulfur chlorotetrafluoride with a fluoride source, such as ZnF2, HF, and Sb(III/V) fluorides. The intermediate arylsulfur chlorotetrafluorides were isolated by distillation or recrystallization and characterized. The aspects of these new reactions are revealed and reaction mechanisms are discussed. As the method offers considerable improvement over previous methods in cost, yield, practicality, applicability, and large-scale production, the new processes described here can be employed as the first practical methods for the economical production of various arylsulfur pentafluorides and their higher homologues, which could then open up a new era of "super-trifluoromethyl" arene chemistry and its applications in many areas.
IMDOLIZINE DERIVATIVES AS LIGANDS OF THE CRTH2 RECEPTOR
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Page/Page column 37, (2008/06/13)
Compounds of formula (I) are CRTH2 antagonists, useful in the treatment of, for example, asthma, chronic obstructive pulmonary disease, rhinitis, allergic airway syndrome, and allergic rhinobronchitis. Formula (I) wherein R1, R2. R3 and R4 each independently are hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, halo, -S(O)nR10, -SO2N(R10)2, -N(R10)2, -C(O)N(R10)2, -NR10C(O)R9, -CO2R10, -C(O)R9, -NO2, -CN or -OR11; wherein each R9 is independently C1-C6alkyl, aryl, heteroaryl; R10 is independently hydrogen, C1-C6alkyl, aryl, or heteroaryl; R11 is hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl or a group -SO2R10 ; n is 0, 1 or 2; R5 is C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, optionally substituted aryl, or optionally substituted heteroaryl; R6 is hydrogen, C1-C6alkyl or fully or partially fluorinated C1-C6alkyl ; R7 and R8 are independently hydrogen or C1-C6alkyl, or R7 and R8 together with the atom to which they are attached form a cycloalkyl group; and X is -CHR6-, -S(O)n-, -C(O)-, -NR6SO2- or -SO2NR6- wherein n is 0, 1 or 2.
New and more potent antifungal bisulfides
Baerlocher, Felix Jakob,Baerlocher, Mark Otto,Langler, Richard Francis,MacQuarrie, Stephanie Lee,Marchand, Maurice Emile
, p. 1 - 5 (2007/10/03)
From a design principle described in an earlier paper, a new series of substituted aryl methyl disulfides have been prepared and tested against Aspergillus niger and Aspergillus flavus. Methyl p-nitrophenyl disulfide is more potent (by an order of magnitude) than the fungitoxic natural product (CH3SCH2S)2. With the present rationale in hand, one can anticipate which Polycarpamine is an effective antifungal agent. CSIRO 2000.
