- Reaction of 2-phenyl-4-(ethoxymethylene)-5(4H)-oxazolone with 3,4-dithio-toluene in the presence of Lewis base
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A convenient procedure for the synthesis of thiocoumarin by the condensation of 2-phenyl-4-(ethoxymethylene)-5-(4H)-oxazolone with 3,4-dithio-toluene in the presence of triethylamine is reported. Here, both thio groups are able to react with the carbonyl group to produce a mixture of isomeric products at ambient temperature. Only one of the isomers upon heating gives a new coumarin product.
- Tikdari, Ahmad Momeni,Hamidian, Hooshang,Razee, Saeid
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p. 2821 - 2826
(2007/10/03)
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- Oxidation of Thiols by Superoxide Ion
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Superoxide ion oxidizes aromatic thiols to disulfides or sulfonic acids.Benzene-1,2-dithiol and its 4-methyl analogue formed the cyclic disulfides dibenzotetrathiocins.Aliphatic thiols gave disulfides, and ethane-1,2-dithiol and propane-1,3-dithiol formed the cyclic disulfides 1,2,5,6- tetrathiocan and 1,2,6,7-tetrathiecan respectively.Butane-1,4-dithiol underwent an intramolecular cyclization to 1,2-dithian.Cysteine was oxidized by O2 anion radical to cysteic acid.
- Crank, George,Makin, Mohammad I. H.
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p. 2331 - 2337
(2007/10/02)
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- Organic chemistry of superoxide. I. Oxidations of aromatic compounds.
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Potassium superoxide is a selective oxidant for aromatic compounds with the order of susceptibility of substituent groups being -SH>-NH2-OH. Only o- and p- disubstituted amines and phenols are oxidized but monosubstituted thiols react.
- Crank,Makin
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p. 2169 - 2170
(2007/10/05)
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