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• W2949205924 endingPage "8008" @default.
• W2949205924 startingPage "8001" @default.
• W2949205924 abstract "Evidence for a Michael addition of a nucleophile to alkenyl(phenyl)iodonium salts at the Cβ atom is reported here for the first time. Nucleophilic vinylic substitutions of (Z)-(β-chloroalkenyl)- 2b and (Z)-(β-bromoalkenyl)iodonium tetrafluoroborates 3b with sodium benzenesulfinate in THF afforded stereoselectively (Z)-1,2-bis(benzenesulfonyl)alkene 5b with retention of configuration. Intermediate formation of (Z)-(β-(benzenesulfonyl)alkenyl)iodonium salt 9b in these reactions was established by 1H NMR experiments in CDCl3. The formation of (Z)-9b involves a hitherto unobserved Michael addition of benzenesulfinate anion to the alkenyliodonium salts at the Cβ atom, followed by halogen extrusion. The formation of a stereoisomeric mixture of (Z)- and (E)-bis-sulfones 5b, and 1-(benzenesulfonyl)cyclopentene 11 that was observed in the reaction of (Z)-(β-fluoroalkenyl)iodonium salt 4b in CDCl3, strongly suggests the intermediacy of 9b in this nucleophilic vinylic substitution." @default.
• W2949205924 created "2019-06-27" @default.
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• W2949205924 date "1997-11-01" @default.
• W2949205924 modified "2023-09-27" @default.
• W2949205924 title "Nucleophilic Vinylic Substitutions of (<i>Z</i>)-(β-Haloalkenyl)phenyliodonium Salts with Sodium Benzenesulfinate: First Evidence of a Michael Addition of Nucleophiles to Alkenyliodonium Salts at the C_β Atom" @default.
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• W2949205924 doi "https://doi.org/10.1021/jo970735v" @default.
• W2949205924 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11671903" @default.
• W2949205924 hasPublicationYear "1997" @default.
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