51290-79-0Relevant articles and documents
Dual Mechanisms of Bimolecular Nucleophilic Subtitution of a Heterobenzylic Bromide Related to Thiamin
Zoltewicz, John A.,Uray, Georg
, p. 1370 - 1375 (1989)
4-Amino-5-(bromomethyl)-1,2-dimethylpyrimidinium ion at 25 deg C in 0.9 M KCl made to an ionic strength of 1 M with buffers react with hydroxide ion with a rate constant 725 M-1s-1.Evidence for an intermediate is found in the large common ion rate retarding effect of added bromide ion.An addition-elimination mechanism (SN(AE)) involving the addition of hydroxide ion to give a pseudobase intermediate followed by loss of bromide ion is advanced.Chloride ion reacts by an SN2 mechanism (5.9E-5 M-1s-1).When 2-thiopyridone acts as a nucleophile by the SN2 mechanism, its sulfur atom is heterobenzylated with a rate constant of 0.28 M-1s-1 (31 deg C).Two different bimolecular mechanisms of nucleophilic substitution are thereby observed.
Synthesis method of heteroaryl thioether
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Paragraph 0019-0022, (2020/08/30)
The invention discloses a synthesis method of heteroaryl thioether. Under the conditions of no catalyst, no solvent, no additive and the like, aryl halide/2-bromopyridine, thiourea and substituted benzyl bromide which are directly taken as raw materials to selectively synthesize asymmetric heteroaryl thioether in one step without using conventional organic sulfides such as mercaptan or thiophenol.The use of organic sulfides with high toxicity and heavy odor, such as mercaptan or thiophenol, is avoided, and the synthesis steps are shortened, so that the synthesis efficiency is improved, the reaction has good selectivity, and the asymmetric thioether can be preferentially obtained.
Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol
Ma, Xiantao,Yu, Jing,Yan, Ran,Yan, Mengli,Xu, Qing
supporting information, p. 11294 - 11300 (2019/09/12)
It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.