18673-13-7Relevant academic research and scientific papers
Thia-Michael addition using cheap and odorless S-alkylisothiouronium salts as thiol equivalents in water
Zhao, Yan,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
, p. 1529 - 1532 (2007)
S-Alkylisothiouronium salt has been found to be a non-toxic, odorless and simply operational alternative of thiol for the thia-Michael addition with electron-deficient olefins. The reactions were carried out under alkaline conditions in water at room temperature within 5-20 minutes to afford the expected products in good to excellent yields. Georg Thieme Verlag Stuttgart.
Novel atom-economic reaction: Comprehensive utilization of S-alkylisothiouronium salt in the synthesis of thioethers and guanidinium salts
Gao, Pengchao,Leng, Penglin,Sun, Qi,Wang, Xin,Ge, Zemei,Li, Runtao
, p. 17150 - 17155 (2013/09/24)
A novel atom-economic three-component one-pot reaction of a primary amine, an S-alkylisothiouronium salt and a Michael receptor is reported, which affords a guanidinium salt and thioether simultaneously. The guanidine moiety is involved in catalyzing the conjugated Michael addition of the mercaptan. The reaction proceeds under ambient conditions using a non-toxic EtOH-H2O mixture as the solvent, and the two products can be very easily purified. Complete atom economy is achieved by fully utilizing the S-alkylisothiouronium salt and converting the previously wasted mercaptan by-product into the valuable thioether.
Borax as an efficient metal-free catalyst for hetero-Michael reactions in an aqueous medium
Hussain, Sahid,Bharadwaj, Saitanya K.,Chaudhuri, Mihir K.,Kalita, Harjyoti
, p. 374 - 378 (2007/10/03)
Borax, a naturally occurring material, very efficiently catalyzed the conjugate addition of thiols, dithiols and amines to α,β-unsaturated ketones, nitriles, amides, aldehydes and esters in an aqueous medium to afford the corresponding Michael adducts in good yields at room temperature. Recycling of the catalyst and scaling up of the reactions are important attributes of this catalysis. The reactions of thiols and dithiols were relatively more facile than those of the corresponding amines. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water
Khatik, Gopal L.,Kumar, Raj,Chakraborti, Asit K.
, p. 2433 - 2436 (2007/10/03)
Catalyst-free conjugate addition of thiols to α,β-unsaturated carbonyl compounds in water is reported. β-Sulfido carbonyl compounds were formed at room temperature, in short times and with excellent chemoselectivity. Competitive dithiane/dithiolane format
CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
, p. 1583 - 1589 (2007/10/03)
Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile
Shah, Syed Tasadaque Ali,Khan, Khalid Mohammed,Martinez Heinrich, Angelica,Voelter, Wolfgang
, p. 8281 - 8283 (2007/10/03)
It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.
Alkylthioalkanoyloxyalkyl and alkylthioalkyl substituted bis-hydantoin compounds
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, (2008/06/13)
Alkylthioalkanoyloxyalkyl and alkylthioalkyl derivatives of N-heterocyclic moieties are stabilizers for organic materials subject to oxidative, thermal and/or light induced deterioration. They are prepared by classical transesterification, oxirane ring opening and addition of mercaptan to olefin reactions. Typical embodiments are tris[2-(3-n-dodecythiopropionyloxy)ethyl isocyanurate] and 3-(3-n-dodecylthio-2-hydroxypropyl)-5,5-dimethylhydantoin. These compounds are used in conjunction with phenolic antioxidants to stabilize organic materials, particularly polyolefins and hydrocarbon compositions, against the deleterious effects of heat and oxygen and against discoloration.
