- A novel method for the synthesis of thiols from the corresponding olefins by using thiocarbonates and Ti(IV) halides
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A convenient method for the preparation of secondary or tertiary thiols from the corresponding olefins was established by using thiocarbonate, titanium(IV) chloride or fluoride and copper(II) oxide. Various thiols were obtained regioselectively in good to excellent yields according to the Markovnikov rule.
- Mukaiyama, Teruaki,Saitoh, Terunobu,Jona, Hideki
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- Structure-odor correlations in homologous series of alkanethiols and attempts to predict odor thresholds by 3d-qsar studies
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Homologous series of alkane-1-thiols, alkane-2-thiols, alkane-3-thiols, 2-methylalkane-1-thiols, 2-methylalkane-3-thiols, 2-methylalkane-2-thiols, and alkane-1,??-dithiols were synthesized to study the influence of structural changes on odor qualities and odor thresholds. In particular, the odor thresholds were strongly influenced by steric effects: In all homologous series a minimum was observed for thiols with five to seven carbon atoms, whereas increasing the chain length led to an exponential increase in the odor threshold. Tertiary alkanethiols revealed clearly lower odor thresholds than found for primary or secondary thiols, whereas neither a second mercapto group in the molecule nor an additional methyl substitution lowered the threshold. To investigate the impact of the SH group, odor thresholds and odor qualities of thiols were compared to those of the corresponding alcohols and (methylthio)alkanes. Replacement of the SH group by an OH group as well as S-methylation of the thiols significantly increased the odor thresholds. By using comparative molecular field analysis, a 3D quantitative structure-activity relationship model was created, which was able to simulate the odor thresholds of alkanethiols in good agreement with the experimental results. NMR and mass spectrometric data for 46 sulfur-containing compounds are additionally supplied.
- Polster, Johannes,Schieberle, Peter
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p. 1419 - 1432
(2015/03/05)
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- Reaction Products and Process of 2-Chloroethyl Ethyl Sulfide in Microemulsion Media
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The reaction of 2-chloroethyl ethyl sulfide was investigated in several oil-in-water microemulsions. The reaction products were identified by GC/MS, NMR, and LC/MS, and the reaction process was monitored by measuring peak height of reaction products and 2-chloroethyl ethyl sulfide with time by 1H NMR spectroscopy. The result showed that 2-chloroethyl ethyl sulfide degraded to 2-hydroxyethyl ethyl sulfide, cyclic sulfonium ion, open chain sulfonium chloro ion and sulfonium hydroxyl ion, and the reaction proceeded via a cyclic sulfonium ion intermediate. Based on the NMR results, a pseudoternary model was established for the reaction process of 2-chloroethyl ethyl sulfide in microemulsion.
- Mei-Ling, Lei,Hai-Ling, Xi,Ming, Shen,Ling, Yuan,Shi-Tong, Han
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p. 387 - 393
(2014/03/21)
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- An Evaluation of Hofmann and Cope Elimination Routes to (+/-)-2-n-Propylthietane
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A synthetic route to (+/-)2-n-propylthietane 1 that utilises a silver oxide-induced Hofmann elimination is described together with an evaluation of the potential of a Cope elimination as an alternative and more costeffective route to 1.Some chemistry of the isomeric intermediate thiete sulfones 5 and 12 from each of these respective eliminations is presented.
- Woolhouse, A. D.,Gainsford, G. J.,Crump, D. R.
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p. 873 - 880
(2007/10/02)
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