76170-43-9Relevant academic research and scientific papers
Functionalization of alkenes by polyfluorinated α,β-unsaturated sulfenyl chlorides: reactions of 2-chloroperfluoro-1-cyclohexene-sulfenyl chloride-1 with activated olefins
Popkova, V. Ya.,Osmanov, V. K.,Borisov, A. V.,Lutsenko, A. I.,Aerov, A. F.,et al.
, p. 181 - 188 (1993)
A variety of β-chlorothioethers have been obtained by the reaction of 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1 (I) with t-butylethene, styrene, allylbenzene and p-methoxyallylbenzene in CH2Cl2 or CH3NO2.Skeletal rearrangement with 1,2-migration of the p-methoxyphenyl group occurs on reaction of I with p-methoxyallylbenzene along with the formation of addition products (Markovnikov and anti-Markovnikov adducts).A possible additive salt effect (LiClO4/CH3NO2 system) has been examined for the reaction of I with t-butylethene, allylbenzene and p-methoxyallylbenzene; the effect is noted only in the case of t-butylethene, when intramolecular rearrangement with 1,2-migration of the methyl group takes place.
Functionalization of alkenes by polyfluorinated α,β-unsaturated sulphenyl chlorides: Dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chloride in reactions with activated olefins
Popkova,Osmanov,Borisov,Ugrak,Bodrikov
, p. 183 - 191 (1996)
A dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chloride (1) in reactions with alkenes is described. Whereas 1 interacts with 3,3-dimethyl-l-butene and styrene in nitromethane solution in the sulphenyl chloride form, reactions with olefins that have mobile hydrogen atoms in an allylic position (e.g. allyl-and p-methoxyallyl-benzenes) occur through the tautomeric thioketone form - 2-chloroper-fluoro-2-methylpentanethione-3 (3) - with the formation of products by ene rearrangement. Chlorotropism in the system 1 ? 3 in the presence of nucleophilic solvents or catalysts is responsible for the dual reactivity of 1 in the above reactions.
