15482-60-7Relevant articles and documents
THIYLATING EFFECT OF 2-CHLORO-2-THIONO-5-METHYL-1,2-OXAPHOSPHOLANE
Nuretdinova, O. N.,Guseva, F. F.
, p. 1423 - 1424 (1991)
It was found that 2-chloro-2-thiono-5-methyl-1,2-oxaphospholane has a thiylating effect toward some compounds with carbonyl and phosphoryl groups.
Enthalpies of combustion of thiobenzamide, N,N-dimethylthiobenzamide, and N,N-diethylthiobenzamide
Silva, Maria D. M. C. Ribeiro da,Souza, Pilar,Pilcher, Geoffrey
, p. 173 - 178 (1989)
The standard (p0 = 0.1 MPa) molar enthalpies of combustion in oxygen at 298.15 K of crystalline thiobenzamide, N,N-dimethylthiobenzamide, and N,N-diethylthiobenzamide to produce CO2(g), N2(g), and H2SO4*115H2O(l) were measured by rotating-bomb calorimetry.The standard molar enthalpies of sublimation at 298.15 K were measured by microcalorimetry. These results form the basis of a bond-energy scheme to estimate ΔfH0m(C6H5CSNR2, g).
Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
Chen, Xinzhi,Ge, Xin,Jin, Hao,Qian, Chao,Zhou, Shaodong
supporting information, p. 3403 - 3406 (2021/06/25)
A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.
Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions
Zhou, Jingwei,Wang, Songping,Lu, Yaoming,Li, Lamei,Duan, Wentao,Wang, Qi,Wang, Hong,Wei, Wentao
supporting information, p. 767 - 773 (2021/02/09)
Due to the particularity of the thiocarbonyl group (C S bond), only limited C(sp3)-H thiocarbonylation methods, especially efficient and convenient methods, have been developed for the synthesis of thioamides. Inspired by the “solvent-specifici
Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur
Peng, Ling,Ma, Li,Ran, Ying,Chen, Yunfeng,Zeng, Zhigang
supporting information, (2021/05/05)
A metal-free C[dbnd]C bond cleavage reaction of β-nitrostyrenes in the presence of elemental sulfur and secondary amines/amides is described. Elemental sulfur serves as both a raw material and an oxidant for C[dbnd]C bond cleavage, and secondary amines or amides are both feasible nitrogen sources. Besides mild reaction condition and simple work-up procedure, the method provided thioamides with good to excellent yields.
Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF
Zhang, Jin,Liu, Ying,Jia, Qiangqiang,Wang, Yue,Ma, Yangmin,Szostak, Michal
supporting information, p. 6884 - 6890 (2020/09/15)
We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.
An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters
Matsumoto, Yohei,Nakatake, Daiki,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 6062 - 6066 (2018/03/28)
A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.
K2S2O8-promoted aryl thioamides synthesis from aryl aldehydes using thiourea as the sulfur source
Bian, Yongjun,Qu, Xingyu,Chen, Yongqiang,Li, Jun,Liu, Leng
, (2018/09/10)
Thiourea as a sulfur atom transfer reagent was applied for the synthesis of aryl thioamides through a three-component coupling reaction with aryl aldehydes and N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC). The reaction could tolerate various functional groups and gave moderate to good yields of desired products under the transition-metal-free condition.
Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S8 and Amides Leading to Aryl Thioamides
Xu, Kai,Li, Ziyi,Cheng, Fangyuan,Zuo, Zhenzhen,Wang, Tao,Wang, Mincan,Liu, Lantao
supporting information, p. 2228 - 2231 (2018/04/30)
A novel transition-metal-free cleavage reaction of C-C triple bonds in aromatic alkynes with S8 and amides furnishes aryl thioamides in moderate to excellent yields. The remarkable features of this thioamidation include the metal-free cleavage of C-C triple bond, mild reaction conditions, as well as wide substrate scope that is particularly compatible with some internal aromatic alkynes and acetamides.
Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon
Kutsumura, Noriki,Ohshita, Ryuichiro,Horiuchi, Jumpei,Tateno, Kotaro,Yamamoto, Naoshi,Saitoh, Tsuyoshi,Nagumo, Yasuyuki,Kawai, Hidetoshi,Nagase, Hiroshi
, p. 5214 - 5219 (2017/07/28)
The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.
