- Electrogeneration of (Z)-α-aroyloxy-β-aroylthiostilbenes and (Z)-4,5-diaryl-2-arylimino-1,3-oxathioles by cathodic reduction of monothiobenzils in the presence of electrophilic reagents. Computational B3LYP and RI-MP2 study on the relative stability of ox
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Electrochemical reductions of monothiobenzils in the presence of either aroyl or carbonimidoyl dichlorides were carried out, yielding products with sulfur retention. Electrolyses in the presence of aroyl chlorides led to previously unknown (Z)-α-aroyloxy-
- Guirado, Antonio,Zapata, Andrés,Andreu, Raquel,López Sánchez, José I.,Paredes, María D.,López Sánchez, Juan E.,Bautista, Delia,Jones, Peter G.,Gálvez, Jesús
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experimental part
p. 1083 - 1090
(2011/03/22)
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- Reactions of Monothiobenzil and its Dimer
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In contrast to the usual formation of monothiobenzil from desyl thiosulfate in a two-phase system involving aqueous sodium hydroxide and methylene chloride, the dimer, 2,4-dibenzoyl-2,4-diphenyl-1,3-dithietane, is obtained in the absence of methylene chloride; and didesyl sulfide is obtained in ethanolic sodium hydroxide-methylene chloride.Thermolysis of monothiobenzil or monothioanisil gives 1,2,3,4-tetraaryl-2-butene-1,4-diones which may be accompanied by benzil or anisil.Monothiobenzil forms an unstable adduct with cyclopentadiene which can be converted to a stable dibromo derivative; it is converted to benzil by treatment with peracide or nitric acid.Dibenzoylstilbene is obtained by thermolysis of the dimer of monothiobenzil or by treatment of the dimer with triphenylphosphine.Treatment of the dimer with Cleland's reagent (2,3-dihydroxy-1,4-butanedithiol) gives didesyl sulfide, and treatment with cyanide ion gives 2-benzoyl-2,4,5-triphenyl-1,3-oxathiole.
- Hartnedy, Richard C.,Dittmer, Donald C.
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p. 4752 - 4754
(2007/10/02)
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- Organic Sulfur Compounds, XLVII Dimerization of Monothiobenzil to a 1,3-Dithietane and its Cycloreversion
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The thermal dimerization of monothiobenzil (1c) to a 1,3-dithietane (2c) and the photochemical cycloreversion of this heterocycle to 1c is described. - Keywords: Heterocycles, Organic Sulfur Compounds, α-Oxothiones, 1,3-Dithietanes, 1,3-Oxathiols, Photore
- Bak, Claudia,Praefcke, Klaus
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p. 372 - 375
(2007/10/02)
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