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- Title
Efficient Regioselective Synthesis of Novel Ensembles of Organylselanyl-Functionalized Divinyl Sulfides and 1,3-Thiaselenoles under Phase Transfer Catalysis Conditions.
- Authors
Filippov, Andrey S.; Amosova, Svetlana V.; Makhaeva, Nataliya A.; Albanov, Alexander I.; Potapov, Vladimir A.
- Abstract
Efficient regioselective synthesis of novel ensembles of organylselanyl-functionalized 1,3-thiaselenoles and divinyl sulfides in high yields under phase transfer catalysis conditions was developed. The methodology is based on the generation of sodium [(Z)-2-(vinylsulfanyl)ethenyl]selenolate and 1,3-thiaselenol-2-ylmethylselenolate, which were involved in a nucleophilic addition reaction with activated alkenes such as acrylonitrile, acrylamide, methyl vinyl ketone, methyl, and ethyl acrylates. In the case of methyl vinyl ketone, the reaction was accompanied by the hydrogenation of the carbonyl group. Methylene chloride was involved in the nucleophilic substitution reaction with sodium [(Z)-2-(vinylsulfanyl)ethenyl]selenolate and 1,3-thiaselenol-2-ylmethylselenolate to afford new polyunsaturated compounds with several sulfur and selenium atoms.
- Subjects
PHASE-transfer catalysis; DIVINYL sulfide; METHYL vinyl ketone; NUCLEOPHILIC substitution reactions; POLYENES
- Publication
Catalysts (2073-4344), 2023, Vol 13, Issue 8, p1227
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal13081227