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• W2075339968 endingPage "1374" @default.
• W2075339968 startingPage "1368" @default.
• W2075339968 abstract "Sulfenic acids (RSOH) are among the most common sulfur-centered reactive intermediates generated in biological systems. Given the biological occurrence of sulfenic acids, it is important to explore the reactivity of these intermediates under physiological conditions. The Morin rearrangement is a synthetic process developed for the conversion of penicillin derivatives into cephalosporins that proceeds via nucleophilic attack of an alkene on a sulfenic acid intermediate. In its classic form, the Morin reaction involves initial elimination of a sulfenic acid from a cyclic sulfoxide, followed by intramolecular cyclization of the resulting alkene and sulfenic acid groups to generate an episulfonium ion intermediate that undergoes further reaction to yield ring-expanded products. On the basis of the existing literature, it is difficult to assess whether the reaction between an alkene and a sulfenic group can occur under mild conditions because the conditions required to generate the sulfenic acid from the sulfoxide precursor in the Morin reaction typically involve high temperatures and strong acid. In the work described here, beta-sulfinylketone precursors were used to generate a Morin type sulfenic acid intermediate under mild conditions. This approach made it possible to demonstrate that the intramolecular cyclization of an alkene with a phenylsulfenic acid to generate an episulfonium ion intermediate can occur in neutral aqueous solution at room temperature." @default.
• W2075339968 created "2016-06-24" @default.
• W2075339968 creator A5008943369 @default.
• W2075339968 creator A5013602438 @default.
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• W2075339968 date "2008-05-23" @default.
• W2075339968 modified "2023-10-16" @default.
• W2075339968 title "Evidence for a Morin Type Intramolecular Cyclization of an Alkene with a Phenylsulfenic Acid Group in Neutral Aqueous Solution" @default.
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• W2075339968 doi "https://doi.org/10.1021/tx8000187" @default.
• W2075339968 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2748810" @default.
• W2075339968 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18500784" @default.
• W2075339968 hasPublicationYear "2008" @default.
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