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2622-21-1

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2622-21-1 Usage

Chemical Properties

Vinylcyclohex-1-ene is a flammable liquid.

Uses

Vinylcyclohex-1-ene is a common component of tobacco smoke thought to be formed by dimerization from butadiene (119). It serves as an important chemical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1946, 1980 DOI: 10.1021/jo01298a037Tetrahedron Letters, 25, p. 5469, 1984 DOI: 10.1016/S0040-4039(01)81601-4

Check Digit Verification of cas no

The CAS Registry Mumber 2622-21-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,2 and 2 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2622-21:
(6*2)+(5*6)+(4*2)+(3*2)+(2*2)+(1*1)=61
61 % 10 = 1
So 2622-21-1 is a valid CAS Registry Number.
InChI:InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2,6H,1,3-5,7H2

2622-21-1Relevant articles and documents

Diels-Alder reactions of masked o-benzoquinones with 1-vinylcyclohexenes: A short and efficient entry to highly functionalized decahydrophenanthrene skeleton

Niu, Guang-Hao,Hou, Chieh-Shen,Chuang, Gary Jing,Wu, Chi-Phi,Liao, Chun-Chen

, p. 3794 - 3801 (2014)

Masked o-benzoquinones (MOBs), which were generated in situ from 2-methoxyphenols, underwent Diels-Alder reactions with 1-vinylcyclohexenes to produce the corresponding cycloaddition products, that is, decahydrophenanthrenes along with bicyclo[2.2.2]octenones. In the former case, the MOBs serve as the dienophile, and in the later case, the 1-vinylcyclohexenes act as the dienophile. The obtained bicyclo[2.2.2]octenones could be transformed into the corresponding decahydrophenanthrenes through a Cope rearrangement at 220 °C. Thus, these tandem reactions provide a short and efficient entry to the decahydrophenanthrene skeleton from easily available 2-methoxyphenols. Masked o-benzoquinones (MOBs), which were generated in situ from 2-methoxyphenols, underwent Diels-Alder reactions with 1-vinylcyclohexenes to produce the corresponding decahydrophenanthrenes and bicyclo[2.2.2]octenones. The obtained bicyclo[2.2.2]octenones could be transformed into decahydrophenanthrenes through a Cope rearrangement at 220 °C. Copyright

Interception of nazarov reactions of allenyl vinyl ketones with dienes: (3+2)- Versus (4+3)-cycloaddition and subsequent rearrangement

Morgan, Timothy D. R.,Lefort, Fran?ois M.,Li, Zhe,Marx, Vanessa M.,Boyd, Russell J.,Burnell, D. Jean

, p. 2952 - 2959 (2015)

Capture of the cyclic oxyallyl cation intermediates from the BF3-mediated Nazarov reactions of three allenyl vinyl ketones with various dienes was accomplished by (3+2)- and (4+3)-cycloaddition. The relative amounts of these types of products were dependent on the substitution on the diene, and this could be linked to steric hindrance. Treatment of the (3+2)-cycloaddition products with BF3·Et2O led mainly to decomposition but also to ring-opened molecules and ring-enlarged structures. The computed Gibbs energies of the (3+2)-cycloaddition products, the products of the acid treatment and of some transition states leading to rearranged products were compared.

Highly selective semi-hydrogenation of alkynes with a Pd nanocatalyst modified with sulfide-based solid-phase ligands

Huang, Lingqi,Hu, Kecheng,Ye, Ganggang,Ye, Zhibin

, (2021/03/30)

Soluble small molecular/polymeric ligands are often used in Pd-catalyzed semi-hydrogenation of alkynes as an efficient strategy to improve the selectivity of targeted alkene products. The use of soluble ligands requires their thorough removal from the reaction products, which adds significant extra costs. In the paper, commercially available, inexpensive, metallic sulfide-based solid-phase ligands (SPL8-4 and SPL8-6) are demonstrated as simple yet high-performance insoluble ligands for a heterogeneous Pd nanocatalyst (Pd@CaCO3) toward the semi-hydrogenation of alkynes. Based on the reactions with a range of terminal and internal alkyne substrates, the use of the solid-phase ligands has been shown to markedly enhance the selectivity of the desired alkene products by efficiently suppressing over-hydrogenation and isomerization side reactions, even during the long extension of the reactions following full substrate conversion. A proper increase in the dosage or a reduction in the average size of the solid-phase ligands enhances such effects. With their insoluble nature, the solid-phase ligands have the distinct advantage in their simple, convenient recycling and reuse while without contaminating the products. A ten-cycle reusability test with the SPL8-4/Pd@CaCO3 catalyst system confirms its well-maintained activity and selectivity over repeated uses. A mechanistic study with x-ray photoelectron spectroscopy indicates that the solid-phase ligands have electronic interactions with Pd in the supported catalyst, contributing to inhibit the binding and further reaction of the alkene products. This is the first demonstration of solid-phase ligands for highly selective semi-hydrogenation of alkynes, which show strong promise for commercial applications.

Piperazine-promoted gold-catalyzed hydrogenation: The influence of capping ligands

Barbosa, Eduardo C. M.,Camargo, Pedro H. C.,Fiorio, Jhonatan L.,Hashmi, A. Stephen K.,Kikuchi, Danielle K.,Rossi, Liane M.,Rudolph, Matthias

, p. 1996 - 2003 (2020/04/22)

Gold nanoparticles (NPs) combined with Lewis bases, such as piperazine, were found to perform selective hydrogenation reactions via the heterolytic cleavage of H2. Since gold nanoparticles can be prepared by many different methodologies and using different capping ligands, in this study, we investigated the influence of capping ligands adsorbed on gold surfaces on the formation of the gold-ligand interface. Citrate (Citr), poly(vinyl alcohol) (PVA), polyvinylpyrrolidone (PVP), and oleylamine (Oley)-stabilized Au NPs were not activated by piperazine for the hydrogenation of alkynes, but the catalytic activity was greatly enhanced after removing the capping ligands from the gold surface by calcination at 400 °C and the subsequent adsorption of piperazine. Therefore, the capping ligand can limit the catalytic activity if not carefully removed, demonstrating the need of a cleaner surface for a ligand-metal cooperative effect in the activation of H2 for selective semihydrogenation of various alkynes under mild reaction conditions.

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