title: Reaction of 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiethane with N-vinyl compounds.
abstract: The reaction of hexafluorothioacetone dimer (2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithiethane, 1) with vinylamides leads to the rapid formation of [2 + 2] cycloadducts: 4-amino-2,2-bis(trifluoromethyl)thietanes. The reaction proceeds in polar solvents (DMF, DMSO) in the absence of a catalyst at elevated temperature producing the corresponding cycloadducts in 47-86% yield. The reaction of N-vinylimidazole unexpectedly led to the formation of the corresponding 1-(hexafluoroisopropyl)-3-vinyl-1,3-dihydro-2H-imidazole-2-thione (5). The structure of this compound, along with the structures of two new thietanes was confirmed by single crystal X-ray diffraction.
authors.affiliation: DuPont Central Research and Development, Experimental Station, PO Box 80500, Wilmington DE 19880-0500, USA.
authors.forename: Viacheslav A
authors.initials: VA
authors.lastname: Petrov
authors.affiliation: DuPont Corporate Center for Analytical Sciences, Experimental Station, PO Box 80500, Wilmington DE 19880-0500, USA.
authors.forename: Will
authors.initials: W
authors.lastname: Marshall
keywords: 1-(hexafluoroisopropyl)-3-vinyl-1,3-dihydro-2H-imidazole-2-thione; 2,2,4,4-terakis(trifluoromethyl)-1,3-dithiethane; 4-amino-2,2-bis(trifluoromethyl)thietanes; organo-fluorine