100897-81-2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 106-51-4 p-benzoquinone 
• 1755-01-7 endo-Dicyclopentadien 
• 78548-82-0 1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 
• 51175-59-8 norbornenoquinone 

Downstream Products

• 2958-72-7 pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione 
• 2435-32-7 exo-5,8-Methano-4a,5,8,8a-tetrahydro-1,4-naphthochinon-2,3-epoxid 
• 60466-75-3 9-methoxy-1,4-anthraquinone 
• 638222-51-2 5,8-bis(4-diphenylphosphoranylbenzyloxy)-1,4-dihydro-1,4-methanonaphthalene 

Relevant academic research and scientific papers

Solar driven uphill conversion of dicyclopentadiene to cyclopentadiene: An important synthon for energy systems and fine chemicals

The retro Diels-Alder conversion of endo-dicyclopentadiene to cyclopentadiene (Cp)-which is thermodynamically uphill under ambient conditions (ΔG = +9.7 kcal mol-1; values based on computation at 273 K following CBS-QB3 methodology)-was carried out at 175-190 °C in neat state using solar energy. The reaction is thermodynamically favorable at elevated temperature. Considering heat release from the reverse reaction (ΔH = -23.4 kcal mol-1), the energy storage efficiency was computed to be ca. 5.5% with respect to the IR component in concentrated solar radiation. Solar energy was further utilized for preparation of a model 2,5-norbornadiene derivative (75% isolated yield) through the cycloaddition reaction of Cp with 4-phenylbut-3-yn-2-one at 150-185 °C. The norbornadiene-quadricyclane system has been proposed for solar energy storage, and its solar assisted synthesis would help reduce its carbon footprint over its life cycle. Norbornadiene synthesis using solar energy may also be of interest for greener processing of fuels derived from this compound. Cookson's cage ketone, which too has been proposed as an energy storage medium, was additionally synthesized from the Diels-Alder adduct of Cp and p-benzoquinone employing concentrated solar photo-thermochemical conditions. The reaction proceeded rapidly (15 min) and gave the desired product in 96% isolated yield. Besides the above applications, Cp is an important synthon in the preparation of fine chemicals.

Promotion of organic reactions by interfacial hydrogen bonds on hydroxyl group rich nano-solids

Surface hydroxyl group rich nano-structured solids dramatically increase the rate of several organic reactions; such effect is attributed to the formation of interfacial hydrogen bonds between the surface hydroxyl groups and the reactants; this catalytic

The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols

Density functional calculations and experiment were used to examine the mechanism, reactivity, and origin of chirality transfer in monophosphine Au-catalyzed monoallylic diol cyclization reactions. The lowest energy pathway for cyclization involves a two-

Catalyst-free one-pot synthesis of 2,4,6-triaryl-1,4-dihydropyridines in ionic liquid and their catalyzed activity on two simple Diels-Alder reactions

A series of 2,4,6-triaryl-1,4-dihydropyridines bearing a hydroxyl group was synthesized greenly by the cascade aldol/Michael/addition reaction of aromatic aldehyde, acetophenone, and NH4OAc (1:2:excessive) in ionic liquid [BmIm][BF4] without any catalyst. The results of their catalyzed activity on two simple Diels-Alder reactions indicated that this kind of compound containing a poly aryl ring can be used as an effective catalyst on the Diels-Alder reaction. This method, because of its environmental friendliness, simplicity, mild conditions, effectiveness, and lower costs, is suitable for the synthesis of arrays of compounds. Copyright Taylor & Francis Group, LLC.

Enhanced Diels-Alder reactions: on the role of mineral catalysts and microwave irradiation in ionic liquids as recyclable media

This manuscript explores in detail the combined effect of solid supports or microwave irradiation in ionic liquids on a series of Diels-Alder reactions involving 1,3-cyclopentadiene and numerous dienophiles.

Polymeric Phosphine Ligand from Ring-Opening Metathesis Polymerization of a Norbornene Derivative. Applications in the Heck, Sonogashira, and Negishi Reactions

The phosphine-containing polymer 1 is obtained by ruthenium-catalyzed ring-opening metathesis polymerization of the norbornene derivative 2. Polymer 1 is employed as the polymer support in the palladium-catalyzed Heck, Sonogashira, and Negishi reactions,

The synthesis of epi-epoxydon utilising the Baylis-Hillman reaction

(±)-epi-Epoxydon was synthesised by means of a triethylaluminium/tri-n-butylphosphine-catalysed Baylis-Hillman reaction between an O-protected epoxidised hydroxyquinol core and paraformaldehyde, constituting the first application of the Baylis-Hillman reaction to a highly functionalised β-substituted enone.

Eine yttriumhaltige starke Lewis-Saeure zur heterogenen Katalyse der Diels-Alder-Reaktion

Keywords: Diels-Alder-Reaktionen; Heterogene Katalyse; Lewis-Saeuren; Yttriumverbindungen

The 1:1 and 2:1 adducts of cyclopentadiene with p-benzoquinone

The exo-cis isomer (8) of the well-known endo-cis 1:1 adduct (4) of cyclopentadiene and p-benzoquinone has been obtained by heating the endo-cis-anti-cis-endo 2:1 adduct (13) with p-benzoquinone and also by haeting 4 alone.The exo-cis isomer of the 1:1 adduct (11) of cyclopentadiene and p-toluquinone has also been obtained for the first time.Heating of the 2:1 adduct 13 gives a mixture containing the endo-anti-exo isomer 15, the exo-anti-exo isomer 16, and 13.The structures of these two new isomers are assigned on the basis of (i) spectroscopic comparison with 13 and the known endo-syn-endo and endo-syn-exo isomers, 12 and 14; (ii) spectroscopic comparison of the corresponding tetrahydro compounds; and (iii) the conversion of tetrahydro 15 by oxidation and acetylation to the syn-hydroquinone diacetate 28, which is stereoisomeric with the anti-hydroquinone diacetate 25, prepared by similar treatment of tetrahydro 13,14, and 16.It is proposed that interconversion of the 1:1 adducts occurs via dissociation-recombination, interconversion of the tetrahydro 2:1 adducts occurs via enolization, while interconversion of the 2:1 adducts themselves can occur by both routes.