58983-21-4

Upstream product

• 498-15-7 (+)-Δ³-carene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 78-79-5 isoprene 
• 186581-53-3 diazomethane 
• 100523-80-6 4-methyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid 

Downstream Products

• 90536-52-0 5-methyl-cyclohexa-2,4-diene-1,2-dicarboxylic acid 
• 20116-65-8 dimethyl 4-methylphthalate 
• 80683-00-7 (2-Hydroxymethyl-4-methyl-cyclohexa-1,4-dienyl)-methanol 

Relevant academic research and scientific papers

EFFICIENT TRANSFORMATION OF (Z)-BUTENE-1,4-DIOLS TO SUBSTITUTED FURANS WITH PYRIDINIUM CHLOROCHROMATE (PCC)

(Z)-2-Butene-1,4-diols were efficiently converted to the corresponding substituted furans by one step oxidation-dehydration process with pyridinium chlorochromate (PCC).

Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions

Plasticization of PVC was carried out by covalently linking phthalate derivatives via copper-free (thermal) or copper catalyzed azide-alkyne cycloadditions. Di(2-ethylhexyl) phthalate derivatives (DEHP-ether and DEHP-ester) were synthesized and appended to PVC at two different densities. The glass transition temperatures of the modified PVC decreased with increasing content of plasticizer. PVC-DEHP-ether gave lower glass transition temperatures than PVC-DEHP-ester, reflecting the enhanced flexibility of the ether versus ester linker.

Solvate Ionic Liquids as Reaction Media for Electrocyclic Transformations

Solvate ionic liquids (SILs) consisting of lithium bis(trifluoromethylsulfonyl)imide dissolved in tri-or tetraglyme have recently emerged as a novel class of ionic liquids. Herein, the first use of solvate ionic liquids as a replacement for molecular solvents in electrocyclization reactions is reported. The SILs promoted both Diels-Alder and [2+2] cycloaddition reactions, compared to an appropriate molecular solvent, and 5 M lithium perchlorate in diethyl ether. The Gutmann acceptor number (AN) of these solvate ionic liquids has also been determined by 31P NMR spectroscopy to be 26.5, thus being modest Lewis acids.

Isotope effects and the distinction between synchronous, asynchronous, and stepwise Diels-Alder reactions

A variety of symmetrical or nearly symmetrical Diels-Alder reactions are studied by a combination of experimental isotope effects, theoretical calculations, and rate observations. Becke3LYP calculations predicted highly asynchronous transition structures for Diels-Alder reactions of bis(boryl)acetylenes, dialkyl acetylenedicarboxylates, triazolinediones, and dialkyl maleates. Rate observations and kinetic isotope effects are consistent with these predictions, though the experimental support for the calculated structures is notably ambiguous in some cases. A concerted mechanism is supported for the retro-Diels-Alder reaction of norbornene. Overall, Diels-Alder reactions appear to be only very weakly biased toward synchronous transition states.

Catalysis by lithium cation: Lithium trifluoromethanesulfonate as a substitute for lithium perchlorate in cycloadditions

Lithium trifluoromethanesulfonate, an easily accessible lithium salt, is shown to be a safe alternative to lithium perchlorate as a promotor in organic Diels-Alder and hetero Diels-Alder reactions.

Diels-Alder Reaction in the Presence of Zeolite

Cu(I) ion exchanged Y-zeolite catalyzed Diels-Alder reaction of furan, cyclopentadiene, 1,3-cyclohexadiene, isoprene and 2,3-dimethylbutadiene with a series of acrylic and acetylenic dienophiles is reported.The cycloadducts are obtained in high yield and selectivity. - Keywords: Cycloaddition Reactions, Copper(I)-zeolite