Reactions of dimethyl sulphoxide with sulphur electrophiles

Senning, A.

doi:10.1039/c19670000064

Cited by 3 publications

(3 citation statements)

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“…Base sensitive sulfinyl chlorides such as 2,2,2-trichloroethanesulfinyl chloride CCl 3 CH 2 SOCl can be oxidized with dimethyl sulfoxide to the corresponding sulfonyl chloride without loss of HCl [86]. Sodium adamantane-1-sulfinate reacts with thiophosgene in an unexpected fashion to yield tris(adamantan-1-ylsulfonyl)methane, (1-C 10 H 15 SO 2 ) 3 CH [103].…”

Section: Sulfinic Acid Derivativesmentioning

confidence: 98%

“…The intriguing anti-Pummerer reaction which takes place between 2 (and similar sulfenyl chlorides) and aliphatic sulfoxides can be applied to the preparation of elusive unsymmetrical disulfides such as 109 [85,86]. In the case shown bis(chloromethyl) sulfoxide 107 becomes the synthetic equivalent of the non-existent chloromethanethiol.…”

Section: Reactions Of Trichloromethanesulfenyl Chloride With Aliphatimentioning

confidence: 98%

“…The same is true of the analogous 2,4,6-tris(dibromomethylene)-1,3,5-trithiane 233 which fails to give dibromothioketene 51b on pyrolysis; cf. equation (86) [143].…”

Section: Sulfur An Important Element In My Lifementioning

confidence: 99%

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Sulfur, An Important Element in my Life

Senning¹

2003

Sulfur Reports

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Section: Sulfinic Acid Derivativesmentioning

confidence: 98%

Section: Reactions Of Trichloromethanesulfenyl Chloride With Aliphatimentioning

confidence: 98%

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Sulfur, An Important Element in my Life

Senning¹

2003

Sulfur Reports

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Sulphinyl chlorides and sulphinic anhydrides

Tillett

1990

Sulphinic Acids, Esters and Derivatives (1990)

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Synthesis, structure, and oxidation of 3,4‐dihydro‐1,2,5‐benzotrithiepins

Ogawa

Sasaki

Ogasawara

et al. 1995

Heteroatom Chemistry

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Stable benzene-fused polysulfide compounds, 3,4dihydro-l,2,5-benzotrithiepins (la-c), have been prepared, and the structure of la has been determined by X-ray crystallographic analysis. While the electrophilic oxidation of compounds 1 with m-chloroperbenzoic acid gave the cowesponding 3,4-dihydro-l,2,5benzotrithiepin 5-oxides (2) in moderate yields, the oxidation of 1 with N-bromosuccinimide afforded a mixture of 5-oxides 2, unexpected, inseparable 3,4dihydro-l,2,5benzotrithiepin 2,2-dioxides (3), and 3,4dihydro-l,2,5-benzotrithiepin 1 ,I -dioxides (4). Semiempirical PM3 calculations were carried out, and the computed HOMO of la suggested a significant favoring of ebctrophilic reactions at the sulfur atom at the 5-position. The treatment of 5-oxides 2 with acetyl bromide or oxalyl dibromide as halogenating reagents gave 2,2-dioxides 3 and 1,l-dioxides 4, suggesting that an intramolecular halogen transfer from the 5-position (sulfide moiety) to the 1-and 2-positions (disulfide moiety) took place in the reactions.C 1995 VCH Publishers, Inc.

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Reactions of dimethyl sulphoxide with sulphur electrophiles

Cited by 3 publications

References 0 publications

Sulfur, An Important Element in my Life

Sulfur, An Important Element in my Life

Sulphinyl chlorides and sulphinic anhydrides

Synthesis, structure, and oxidation of 3,4‐dihydro‐1,2,5‐benzotrithiepins

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