Die Struktur der Sulfinsäureanhydride

Bredereck, Hellmut; Wagner, Adolf; Beck, H. P.; Klein, R.

doi:10.1002/cber.19600931145

Cited by 47 publications

(7 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1B ), which are high-valent analogs of disulfides, have been known for over a century 26 . However, their structure and reactivity have only been sporadically investigated 27 – 30 ; the perception that sulfinyl sulfones are unstable, hard-to-handle materials, along with a lack of reliable methods for their synthesis, has deterred research and restricted their occasional use as electrophilic sulfur sources 31 – 33 . A single report suggested that their thermal decomposition might proceed via homolytic fission, generating two distinct sulfur-centered radicals—a sulfinyl radical and a sulfonyl radical 34 .…”

Section: Introductionmentioning

confidence: 99%

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

et al. 2021

View full text Add to dashboard Cite

Sulfinyl radicals – one of the fundamental classes of S-centered radicals – have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition/radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

et al. 2021

View full text Add to dashboard Cite

show abstract

“…To our knowledge, no sulfinyl sulfonyl thionahydride derivatives have ever been reported. In contrast, the preparation, characterization, and properties of their disulfide analogs 3 and 4 have been investigated, but the study was somewhat limited by the low stability of this class of compounds …”

mentioning

confidence: 99%

Synthesis and Decomposition of Tri- and Tetraoxide Derivatives of Dialkyl Trisulfides

Derbesy

Harpp

1996

J. Org. Chem.

View full text Add to dashboard Cite

The first isolation and characterization of sulfinyl sulfonyl thioanhydride 1 and its tetrasulfide analog are presented here, along with those of disulfonyl thio- and dithioanhydrides 2. The oxidation of various substrates at different temperatures has shown that, contrary to current belief, oxidation takes place regiospecifically at the external sulfinyl sulfur rather than at the internal sulfenyl sulfur. The decomposition of these compounds has also been investigated and was found to be consistent with the mechanism proposed for the decomposition of trisulfide monoxides.

show abstract

“…1B), which are high-valent analogues of disul des, have been known for over a century 26 . However, their structure and reactivity has only been sporadically investigated [27][28][29][30] ; the perception that sul nyl sulfones are unstable, hard-to-handle materials, along with a lack of reliable methods for their synthesis, has deterred research and restricted their occasional use as electrophilic sulfur sources [31][32][33] . A single report suggested that their thermal decomposition might proceed via homolytic ssion, generating two distinct sulfur-centered radicals-a sul nyl radical and a sulfonyl radical 34 .…”

Section: Main Textmentioning

confidence: 99%

“…Terminal (cyclo)alkyl alkynes provided additional products 3-13 in good yield, whereas the reaction with aryl alkynes resulted in near-quantitative yield, regardless of the steric and electronic properties of the substituents (14-29), with the possible exception of 4-nitrophenylacetylene (23, 75%). Equally productive were a naphthyl and two thienyl alkynes (30)(31)(32). A conjugated enyne was chemoselectively converted into product 33 with the alkene moiety untouched; however, alkynes featuring functional groups sensitive to acetyl chloride (hydroxyl, amino, carboxyl, amide) required the use of preformed sul nyl sulfone 1 (12, 13, 27, and 28).…”

Section: Main Textmentioning

confidence: 99%

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Wang

Zhang

Zhao

et al. 2021

Preprint

View full text Add to dashboard Cite

Sulfinyl radicals – one of the fundamental classes of S-centered radicals – have eluded synthetic application in organic chemistry for over 60 years, despite their potential to assemble valuable sulfoxide compounds. Here we report the successful generation and use of sulfinyl radicals in a dual radical addition / radical coupling with unsaturated hydrocarbons, where readily-accessed sulfinyl sulfones serve as the sulfinyl radical precursor. The strategy provides an entry to a variety of previously inaccessible linear and cyclic disulfurized adducts in a single step, and demonstrates excellent tolerance to an extensive range of hydrocarbons and functional groups. Experimental and theoretical mechanistic investigations suggest that these reactions proceed through sequential sulfonyl and sulfinyl radical addition.

show abstract

Die Struktur der Sulfinsäureanhydride

Cited by 47 publications

References 14 publications

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Synthesis and Decomposition of Tri- and Tetraoxide Derivatives of Dialkyl Trisulfides

Synthetic exploration of sulfinyl radicals using sulfinyl sulfones

Contact Info

Product

Resources

About