Trifluoroethyl sulfenylation or sulfinylation with 2,2,2-trifluoroethyl t-butyl sulfoxide

Redon, Martine; Janousek, Z.; Viehe, H. G.

doi:10.1016/s0040-4020(97)10027-8

Cited by 11 publications

(4 citation statements)

References 14 publications

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“…To our surprise, when sulfoxide 18g bearing a tert -butyl group was employed (Table , entry 3), only the sulfenylated product 22 could be isolated from the reaction mixture (Scheme ). This is likely a consequence of loss of a tert -butyl cation from the activated sulfoxide and concomitant generation of phenylsulfanyl trifluoroacetate, an electrophilic sulfenylating reagent …”

Section: Resultsmentioning

confidence: 99%

Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds

et al. 2013

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Section: Resultsmentioning

confidence: 99%

Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds

et al. 2013

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“…The analogous addition reaction of sulfines is known for amines . The sulfenic acid 8 may then add to the triple bond of cyclooctyne under formation of the sulfoxy group, which is a documented reaction for sulfenic acids …”

mentioning

confidence: 89%

Thermal and Photochemical 1,3-Dipolar Cycloaddition of a Sulfine (Fluorenethione S-Oxide) to the Strained Triple Bond of Cyclooctyne

1998

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“…As a part of a wider study concerning the reactivity of 2,2,2-trifluoroethyl tert-butyl sulfoxide as sulfenylating agent, Viehe et al thermolyze it [31] in the presence of DMAD. The obtainment of dimethyl (E)-2-[(2,2,2-trifluoroethyl)sulfinyl]-2-butenedioate as single pure product with 87% yield is in accordance with the syn-addition of 2,2,2-trifluoroethanesulfenic acid to the triple bond.…”

Section: Transient Sulfenic Acids As Intermedi-ates In Organic Synthesismentioning

confidence: 99%

Recent Advances and Perspectives in the Chemistry of Sulfenic Acids

Aversa¹,

Barattucci²,

Bonaccorsi³

et al. 2007

COC

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This review provides a comprehensive survey of the literature on sulfenic acid chemistry from 1990 through June 2006, focusing the attention on salient aspects of their structures and involvement in organic processes. Even if the majority of known sulfenic acids cannot be isolated, some stable ones have been obtained, and their study helped dramatically the comprehension of chemical and physical properties of all sulfenic acids and indirectly of the role that Cys-SOHs play in protein biochemistry. Many papers have been published in the last fifteen years about the sulfenic acid intermediacy in organic chemistry. Once generated, they can be involved in intra-and intermolecular additions to unsaturated molecules. Few examples of sulfenic acid addition to double bonds have been recently described and most of them are intramolecular processes, whereas the addition of enantiopure sulfenic acids onto carbon-carbon triple bonds has been widely exploited in the synthesis of vinyl sulfoxides to be used in many stereoselective transformations. The thermicelimination from sulfinyl precursors is a way to generate sulfenic acids but it has been also used for removing the sulfinyl moiety from organic molecules and forming double bonds with controlled stereochemistry. Some significant applications of extrusion processes are also described in the present review.

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Trifluoroethyl sulfenylation or sulfinylation with 2,2,2-trifluoroethyl t-butyl sulfoxide

Cited by 11 publications

References 14 publications

Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds

Sulfur(IV)-Mediated Transformations: From Ylide Transfer to Metal-Free Arylation of Carbonyl Compounds

Thermal and Photochemical 1,3-Dipolar Cycloaddition of a Sulfine (Fluorenethione S-Oxide) to the Strained Triple Bond of Cyclooctyne

Recent Advances and Perspectives in the Chemistry of Sulfenic Acids

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