ISSN:
0009-2940
Keywords:
Trifluoromethylsulfanyl compounds
;
Pentafluorophenylsulfanyl compounds
;
Trifluoromethylselenanyl compounds
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Tris(perfluoroorganochalkogenyl)methyl Compounds: Synthesis, Structures, and PropertiesReaction of (CF3S)2CHC(OC2H5)3 with CF3SCl or CF3SeCl in the presence of NaH in ether provides X(CF3S)2CC(O)OC2H5 (1a, b: X = CF3S, CF3Se). These compounds react with NH3 to form (CF3S)2CHC(O)NH2 (2b) which is also obtained from (CF3S)2CHC(O)OC2H5 and NH3. Dehydration of the amide 2b yields (CF3S)2CHCN (3b), which reacts with NaH and then with CF3SX (X = Cl, SCF3) or with RfCl (Rf = CF3Se, C6F5S) to give Rf (CF3S)2CCN [Rf = CF3S (3c), CF3Se (3d), C6F5S (3e)]. 3c is also obtained from (CF3S)3CBr and AgCN. Hydrolysis of 3c with conc. H2SO4 leads almost quantitatively to (CF3S)3CC(O)NH2 (2c), which on treatment with COCl2 gives only 3c and not the corresponding isocyanate. If phosgene is replaced by oxalyl chloride and treated with 2c in a 1:1 molar ratio, (CF3S)3CC(O)NCO (4a) is formed. The urea derivative (CF3S)3CC(O)NHC(O)NHC(O)C(SCF3)3 (4b) is obtained either by using a 2:1 molar ratio of 2c and [C(O)Cl]2 or from 2c and 4a. Attempts to substitute (CF3S)2CHCO2H - after treatment with NaH in ether - with CF3SCl provides low yields of 2,4-bis[bis(trifluoromethylsulfanyl)methylene]-1,3-dithietane (5). X-ray structure analyses are performed for (CF3S)3CCN (3c) and the 1,3-dithietane 5.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270302
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