16245-83-3Relevant academic research and scientific papers
An efficient catalyst-free synthesis of thiiranes from oxiranes using polyethylene glycol as the reaction medium
Das, Biswanath,Reddy, V. Saidi,Krishnaiah
, p. 8471 - 8473 (2006)
A catalyst-free, high-yielding conversion of oxiranes into thiiranes has efficiently been carried out by treatment with KSCN or thiourea at room temperature using polyethylene glycol (PEG-400) as the reaction medium.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
Synthesis of α-aliphatic and β-aromatic substituted taurines via regioselective ring opening of thiiranes with ammonia
Yu, Hao,Cao, Shengli,Zhang, Leilei,Liu, Gang,Xu, Jiaxi
experimental part, p. 2205 - 2209 (2010/02/27)
Thiiranes are important starting materials for the synthesis of substituted taurines. The regioselectivity of ring-opening reactions of thiiranes with ammonia in the presence of silver nitrate was investigated. The results of the ring-opening reaction and subsequent peroxy acid oxidation indicate that alkyl-substituted thiiranes give rise to 1-monoalkyl- and 1,1-dialkyltaurines, whereas aryl-substituted thiiranes produce 2-aryl-, 2-alkyl-2-aryl-, and 2,2-diaryltaurines. This shows that alkyl-substituted thiiranes were attacked on their less-substituted ring carbon atoms, while aryl-substituted thiiranes were attacked on their more substituted ring carbon atoms. The current method is an effective and atom-economic route for the synthesis of mono- and disubstituted α-alkyl-and β-aryl-substituted taurines. Georg Thieme Verlag Stuttgart.
Synthesis of thiiranes from oxiranes in the presence of β-cyclodextrin in water
Srilakshmi Krishnaveni,Surendra,Somi Reddy,Nageswar,Rama Rao
, p. 395 - 397 (2007/10/03)
A mild and highly efficient, user-friendly procedure has been developed for the conversion of oxiranes to thiiranes under supramolecular catalysis in the presence of β-cyclodextrin in water at ambient temperature in excellent yields. The use of β-cyclodextrin in this transformation overcomes the use of heavy metal halides as promoters and chlorinated hydrocarbons and other hazardous organic solvents.
Indium tribromide: A novel and highly efficient reagent for the conversion of oxiranes to thiiranes
Yadav,Reddy,Baishya, Gakul
, p. 396 - 398 (2007/10/03)
Epoxides react smoothly with potassium thiocyanate in the presence of 5 mol% of indium tribromide under mild and convenient reaction conditions to afford the corresponding thiiranes in high yields. This method is compatible with a wide range of protecting groups and functional groups such as alkenes, alkynes, esters, THP, TBDMS, and PMB ethers present in the molecule.
N-bis(methylthio)methylene derivatives. VII. Syntheses and reactions of synthetic equivalents of new 1,3-dipolar reagents using N- bis(methylthio)methylene derivatives
Tominaga,Ogata,Ueda,Kohra,Hosomi
, p. 1425 - 1434 (2007/10/03)
N-Cyano- or N-(p-toluenesulfonyl)-N'-(trimethylsilylmethyl)-S- methylisothioureas (3,4), readily prepared by reactions of S,S'-dimethyl N- cyano- (1a) and S,S'-dimethyl N-(p-toluenesulfonyl)- (1b) carbonimidodithioates with trimethylsilylmethylamine (2a), followed by N- alkylation, have been found to provide synthetic equivalents of iminoazomethine ylide. Treatment of these compounds with cesium fluoride in the presence of reactive heterodipolarophiles such as carbonyl compounds afforded 1,3-dipolar cycloadducts, 4,5-dihydro-2-iminooxazoles and 4,5- dihydro-2-iminothiazoles, via the 1,3-elimination of (methylthio)trimethylsilane. S-Methyl-S'-trimethylsilylmethyl N-cyano- (5a) and N-(p-toluene-sulfonyl)- (5b) carbonimidodithioates, also readily prepared from the corresponding 1a and 1b with (mercaptomethyl)trimethylsilane (2b), were used as new reagents for introducing a thioformaldehyde unit at a carbonyl carbon. Reactions of these compounds with aldehydes in the presence of cesium fluoride afforded thiiranes via the 1,3-dipolar cycloaddition of iminothiocarbonyl ylide to the C=O double bond. Reactions of 5 with dimethyl fumarate and maleate in the presence of cesium fluoride in acetonitrile gave 1,3-dipolar cycloadducts, dimethyl 2-(N-(p- toluenesulfonyl)imino)tetrahydrothiophene-3,4-dicarboxylates.
New synthesis of thiiranes by fluoride ion-promoted reaction of S-methyl-S'-trimethylsilylmethyl N-(p-toluenesulfonyl)dithioiminocarbonate and 2-(trimethylsilylmethylthio)thiazoline with aldehydes
Tominaga,Ueda,Ogata,Kohra,Hojo,Ohkuma,Tomita,Hosomi
, p. 85 - 88 (2007/10/02)
The title compounds, readily prepared by the reaction of the corresponding S-methyl N-(p-toluene-sulfonyl)dithioiminocarbonate and 2-mercaptothiazoline with (chloromethyl)trimethylsilane in the presence of a base, were used as a new reagents for the intro
