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• W2093625453 endingPage "1998" @default.
• W2093625453 startingPage "1989" @default.
• W2093625453 abstract "Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 2. — Formation of Episulfones, Sulfonylsulfene — Amine S.N-Adducts. and Chlorosulfines from Primary Sulfonyl Chlorides and Tertiary Amines The reaction of primary sulfonyl chlorides 1b–m with the tertiary amine bases quinuclidine, DABCO, Me3N, Et3N, Bu3N, EtiPr2N, and 1,2,2,6,6-pentamethylpiperidine is studied in acetonitrile solution between − 40 and 80°C. The 2,3-dialkylthiirane 1,1-dioxides 4 (trans/cis > 1) and the alkenes 5 [(E)/(Z) > 1] are obtained in high yields with Et3N at − 40°C. The stereochemistry is influenced by the amine base B in the ring closure reaction and partially by epimerization of the episulfones 4. Hindered bases favor the cis, β-branched sulfonyl chlorides the trans isomer. Competing formation of the sulfonylsulfene–amine S,N-adducts 7 is only observed with quinuclidine, DABCO, and Me3N, which are also the most active amines in the epimerization of the cis-2,3-diarylthiirane 1,1-dioxides 4. Methanesulfonyl chloride (1a) yields the mesylsulfene–amine S,N-adducts 7a with Me3N and Et3N in MeCN, but thiirane 1,1-dioxide (4a) with EtiPr2N in MeCN or with Et3N in Et2O. Formation of chlorosulfines 10 is favored by higher temperature (T > 20°C), hindered amine bases and β-branched sulfonyl chlorides. Isolation of 10g and 10h in high yields shows that tert-alkylchlorosulfines are rather stable sulfines." @default.
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• W2093625453 date "1990-10-01" @default.
• W2093625453 modified "2023-10-16" @default.
• W2093625453 title "Folgereaktionen von Sulfenen aus Sulfonylchloriden und tertiären Aminen, 2. Bildung von Episulfonen, Sulfonylsulfen — Amin‐S,N‐Addukten und Chlorsulfinen aus primären Sulfonylchloriden und tertiären Aminen" @default.
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• W2093625453 doi "https://doi.org/10.1002/cber.19901231010" @default.
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