870-73-5Relevant academic research and scientific papers
Evidence for heterolytic cleavage of C-S bonds in the photolysis of 1,3,5-trithianes
Hug,Janeba-Bartoszewicz,Filipiak,Pedzinski,Kozubek,Marciniak
, p. 883 - 892 (2008/12/23)
The homolytic/heterolytic nature of photolytic C-S bond cleavage was studied in 1,3,5-trithianes. The mechanism of photolysis was refined from previous studies. First, evidence was presented for the existence of a precursor of the biradical-like transient (I) which itself was identified in previous studies. Second, the nature of I was further clarified through methanol-scavenging experiments where the results could be interpreted as lending credibility to the notion that I has significant bipolar character. Kinetic and spectral analyses of transient absorptions, following laser excitation of the trithianes, showed that I was reacting with methanol. Complementary steady-state photolytic quantum yields supported this finding, and additional, but unidentified, stable products from irradiations in methanol were seen in the HPLC. The formation of these products was interpreted as likely arising from a nucleophilic attack of methanol at the carbocationic end of the bipolar structure of I.
Oxazolidinone photoaffinity probes
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, (2008/06/13)
Disclosed are novel compounds that are useful and effective as photoaffinity probes and methods of using oxazolidinone photoaffinity probes.
A New Preparation of 5-(Alkylthio)-1,2-dithiole-3-thiones and a Highly Functionalized 1,3-Dithiole-2-thione
Lu, F. L.,Keshavarz-K., M.,Srdanov, G.,Jacobson, R. H.,Wudl, F.
, p. 2165 - 2169 (2007/10/02)
A "one-pot" preparation of the title 1,2-dithiole-3-thiones as well as the preparation and characterization of methyl 5-(methylthio)-2-thioxo-1,3-dithiole-4-dithiocarboxylate (3) are described.The X-ray structure determination of an iodine complex of the dithiolodithiole 5 is described in detail.The structure shows that this is a molecular solid with unusual three-dimensional intermolecular sulfur-sulfur "bonding".
2-β-D-RIBOFURANOSYLBENZOXAZOLE FROM 2,5-ANHYDRO-D-ALLONOIMIDATE, AND 1,3-DIMETHYL-8-β-D-RIBOFURANOSYLXANTHINE FROM 2,5-ANHYDRO-D-ALLONO-THIOIMIDATES AND -DITHIOATES
Khadem, Hassan S. El,Kawai, Joshua
, p. 271 - 284 (2007/10/02)
The ability of imidates, thioimidates, and dithioates to react with o-aminophenol (2) and 5,6-diamino-1,3-dimethyluracil (6) was studied, using nonsaccharide model compounds, as well as saccharide derivatives.All of the model compounds gave 2-methylbenzoxazole, but only ethyl dithioacetate gave a purine derivative with 6.Methyl 2,5-anhydro-D-allonoimidate hydrochloride reacted with 2 to yield 2-β-D-ribofuranosylbenzoxazole, but failed to react with compound 6.On reaction with compound 6 such fully acylated thioimidates as ethyl and benzyl 2,5-anhydrotri-O-benzoyl- or tri-O-p-toluoyl-D-allonothioimidate hydrochloride yielded amidines that underwent aromatization of the furanose ring.Such monoacylated thioimidates as ethyl or benzyl 2,5-anhydro-6-O-benzoyl-D-allonothioimidate hydrochloride yielded, with compound 6, 8-(5-O-benzoyl-β-D-ribofuranosyl)-1,3-dimethylxanthine, without aromatization.Such dithioates as benzyl 2,5-anhydro-6-O-benzoyl-D-allonodithioate and ethyl 2,5-anhydrotri-O-benzoyl-D-allonodithioate were obtained by treating the corresponding thioimidate with H2S in pyridine.With compound 6, the first yielded 8-(5-O-benzoyl-β-D-ribofuranosyl)-1,3-dimethylxanthine, which afforded the free C-nucleoside 1,3-dimethyl-8-β-D-ribofuranosylxanthine on treatment with methanolic ammonia.
STUDIES ON ORGANOPHOSPHORUS COMPOUNDS XLVIII Synthesis of Dithioesters from P,S-Containing Reagents and Carboxylic Acids and Their Derivatives
Yousif, N. M.,Pedersen, U.,Yde, B.,Lawesson, S.-O.
, p. 2663 - 2670 (2007/10/02)
2,4-Bismethylthio-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIa, is prepared from O,O-dimethyldithiophosphoric acid, Ia, and P4S10 at 160 deg C. 2,4-Bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIc, and 2,4-bis(4-phenyl-thiolphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IId, are prepared at 160 deg C from P4S10 and diphenylether and diphenylsulfides, respectively.Carboxylic acids RCOOH (R=CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H5) react with compound Ia at 130 deg C to give the corresponding methyl dithioesters.Carboxylic acids RCOOH (R=C6H5-CH2, C6H5) react with compound Ib at 200 deg C for 15 min to give the corresponding ethyl dithioesters, while low boiling acids (R=CH3, C2H5, n-C3H7) yielded mixtures of the corresponding ethyl dithioester and ethyl carboxylate.Carboxylic acid chlorides RCOCl (R=ClCH2, C2H5, t-C4H9, C6H5CH2, C6H5, p-NO2C6H4) react with compound IIa at 80 deg C to give the corresponding methyl dithioesters in good yields.S-Substituted thioesters react with IIc at 85 deg C to give the corresponding dithioesters in good yields.Dihydro-2(3H)-furanone, VI, and 5-methyl-2(3H)-furanone, VII, react with IIa at 80 deg C to give dihydro-2(3H)-thiophenethione, VIII and 2,2'-dithiobis(5-methyl thiophene), IX, respectively.Also XI reacts with IIa, IIc, and IId to give VIII in nearly quantitative yields.
A Direct Conversion of Carboxylic Acids into Dithioesters
Davy, Hubert
, p. 457 - 458 (2007/10/02)
A facile one-pot reaction between carboxylic acids and S-alkyl phosphorus sulphides affords the corresponding alkyl dithioesters.
