26579-97-5

Upstream product

• 67-56-1 methanol 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 90-02-8 salicylaldehyde 
• 105-55-5 N,N'-diethylthiourea 
• 7664-93-9 sulfuric acid 
• 142-45-0 Acetylenedicarboxylic acid 
• 685-63-2 hexafluoro-1,3-butadiene 

Relevant academic research and scientific papers

A convenient synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene)acetate derivatives involving an electrogenerated base of acetonitrile

We report a simple method for the synthesis of alkyl-2-(2-imino-4-oxothiazolidin-5-ylidene) acetate derivatives 3 in good yields under mild conditions. The electrogenerated cyanomethyl base (EGB), obtained from electroreduction of acetonitrile-0.1 M TBABF4, assists the reaction between thiourea derivatives 1 and dialkyl acetylene dicarboxylate 2. The expected products, 3/4, and the structure obtained from X-ray diffraction confirm that the main products are the five-membered heterocycles 3. Furthermore, a mechanism, to explain the reaction pathways, is proposed based on the thermodynamic and kinetic data obtained from quantum calculations.

A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water

The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol

Aqueous-phase deactivation and intramolecular [2 + 2 + 2] cycloaddition of oxanorbornadiene esters

Both inter- and intramolecular degradation pathways were identified for the aqueous phase deactivation of oxanorbornadiene (OND) electrophiles, and propargylic OND esters were found to undergo facile intramolecular [2 + 2 + 2] homo-Diels-Alder cycloaddition in polar media.

Isolable gold(I) complexes having one low-coordinating ligand as catalysts for the selective hydration of substituted alkynes at room temperature without acidic promoters

Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)-phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones in nearly quantitative yields. Acid-labile groups present in the substrates are preserved. The catalytic activity strongly depends on both the nature of the phosphine coordinated to the gold (I) center and the softness of the counteranion, the complex AuSPhOsNTf2 showing the better activity. A plausible mechanism for the hydration of alkynes through ketal intermediates is proposed on the basis of kinetic studies. The described catalytic system should provide an efficient alternative to mercury-based methodologies and be useful in synthetic programs.

The crystal structure of [Mo(NCS)(CO)2(η3-C3H5) (NCMe)2].MeCN and the reactions of {Mo(CO)2 (η3-C3H5)+} containing species with symmetric alkynes

In the solid-state about molybdenum, with carbonyls and nitriles in the equatorial plane and an N-bonded thiocyanate group trans to the allyl ligand. In refluxing methanol or acetonitrile both 1, and the analogous chloro-complex [MoCl(CO)2(η3-C3 H5)(NCMe)2](2) catalytically convert PhC≡CPh to a mixture of hexaphenylbenzene and E,E-1,2,3,4-tetraphenylbutadiene. By contrast MeO2CC≡CCO2Me is not oligomerised. In methanol, complex 2 dimerises 1,4-diphenylbutadiyne to Z,E-1,4,5,8-tetraphenyl-1,7-octa-3,5-diene-1,7-diyne, whereas in the presence of base both the complex and the diyne, react preferentially with the solvent to generate the [Mo2(CO)4 (η3-C3H5)2 (OMe)3]- anion and Z-1,4-diphenyl-3- methoxy-but-3-ene-1-yne, respectively.