The first representatives of ferrocenes containing mesoionic heterocyclic substituents were obtained by the ferrocenyl alkylation of 4-mercapto derivatives of sydnones and sydnone imines. Several synthesized derivatives showed high antidote activity against metsulfuron-methyl (Zinger WP) herbicide.
We have formulated and developed a route for the synthesis of sulfur-containing heterocycles based on the interaction of sulfenyl chlorides with unsaturated compounds which occurs by ring closure at the nucleophilic center of the sulfenyl unit [1-6].In the current work reactions of 3,3-dimethyl-1-butene (1) with the hetarenesulfenyl chlorides 2a-d which contain a potentially nucleophilic nitrogen atom in the hetaryl unit: 4,6-dimethylpyrimidine-2-(2a), 3-cyano-4,6-dimethylpyridine-2-(2b), quinoline-8-(2c), and 1,3-benzothiazole-2-sulfenyl chloride (2d). S-Het Cl N N Me Me N Me Me CN N S N t-Bu 1 + Het-SCl 2a-d t-Bu 2, 3 a Het = b Het = c Het = d Het = , , ,
3a-dWith the help of 1 H NMR spectroscopy it was established that addition products at the double bond contrary to Markovnikov's rule -the corresponding β-chlorosulfides 3a-d -were obtained rapidly and with quantitative yield from compounds 2a-d and the alkene 1 at 20°C.
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