937-00-8Relevant articles and documents
Preparation method of 3-trifluoromethyl benzenethiol and 3-methylthio benzotrifluoride
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Paragraph 0035-0041; 0055-0057, (2019/02/26)
The invention discloses a preparation method of 3-trifluoromethyl benzenethiol and 3-methylthio benzotrifluoride, which belongs to the technical field of chemical synthesis. The invention provides thepreparation method of the 3-trifluoromethyl benzenethio
Catalytic transfer hydrogenation of aryl sulfo compounds
Chen, Xinzhi,Zhou, Shaodong,Qian, Chao
experimental part, p. 179 - 185 (2012/05/21)
A new method to reduce aryl sulfo compounds via transfer hydrogenation was investigated, using Pd/C as a catalyst, and 2-propanol or formic acid as hydrogen sources. This new process is simple and clean.
Solvent-free synthesis of thiophenol using uncatalyzed transfer hydrogenation
Zhou, Shaodong,Qian, Chao,Chen, Xinzhi
experimental part, p. 2432 - 2439 (2012/06/18)
Clean and sustainable transfer hydrogenation for aryl sulfonamides and sulfonyl chlorides is described. The protocol is chemoselective and uses neither catalyst nor solvent.
A general and efficient approach to aryl thiols: Cul-catalyzed coupling of aryl iodides with sulfur and subsequent reduction
Jiang, Yongwen,Qin, Yuxia,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua,Ma, Dawei
supporting information; scheme or table, p. 5250 - 5253 (2009/12/28)
A Cul-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90 °C. The coupling mixture is directly treated with NaBH4 or triphenylphosphine to afford aryl thiols in good to
An efficient synthetic route to aryl thiocyanates from arenesulfinates
Still,Watson
, p. 1355 - 1359 (2007/10/03)
An efficient procedure for the conversion ot the inexpensive and readily available arenesulfinate (sodium) salts in three steps into the corresponding aryl thiocyanates is described. Overall yields are high, and the presence of both electron-with drawing and electron-donating substituents is well tolerated.
Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system
Uchiro, Hiromi,Kobayashi, Susumu
, p. 3179 - 3182 (2007/10/03)
A new and efficient method for the non-aqueous reduction of sulfonyl chlorides to affored the corresponding thiols by use of a dichlorodimethylsilane-zinc-dimethylacetamide system was successfully developed. Various aromatic thiols were prepared in high yield by easy operation. Continuous reactions with the above reduction using the prepared thiol were also demonstrated.
Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues
Reich, Hans J.,Willis, William W.,Clark, Peter D.
, p. 2775 - 2784 (2007/10/02)
A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.
ADDITIONS OF SUBSTITUTED PHENYLTHIYL RADICALS TO SUBSTITUTED α-METHYLSTYRENES. GROUND STATE AND TRANSITION STATE ELECTRONIC EFFECTS
Geers, Brian N.,Gleicher, Gerald Jay,Church, Daniel F.
, p. 997 - 1000 (2007/10/02)
The radical addition of substituted thiophenols to α-methylstyrene and substituted α-methylstyrenes has been investigated at 70 deg C.Relative reactivities of pairs of thiophenols competing with individual alkenes can be utilized to obtain Hammett correlations.The interplay of substituent effects in alkene and thiyl radical leads to examples of non-linear rho values.Rationales for this behavior will be offered in terms of variable contributions from ground state and transition state electronic factors as well as in terms of possible mechanistic changes.
HYDROLYSIS KINETICS AND MECHANISM OF DIARYLTHIOCARBAMATES IN 20percent AQUEOUS DIOXANE MEDIUM
Mindl, Jaromir,Balcarek, Pavel,Silar, Lubomir,Vecera, Miroslav
, p. 3130 - 3139 (2007/10/02)
Substituted S-aryl and O-aryl N-arylthiocarbamates have been synthetized.Kinetic studies of hydrolysis of these compounds in 20percent aqueous dioxane prove the ElcB mechanism.The found Hammett reaction constants, activation entropy values, Broensted coefficients, and comparison of reactivity with N-methyl analogues have been discussed as criteria of the mentioned mechanism.Hydrolysis results of thiocarbamates and carbamates in the same medium are compared.
