1541-20-4

Upstream product

• 110-22-5 diacetyl peroxide 
• 110-83-8 cyclohexene 
• 56-23-5 tetrachloromethane 
• 75-09-2 dichloromethane 
• 67-66-3 chloroform 
• 108-31-6 maleic anhydride 
• 119-61-9 benzophenone 
• 75-07-0 acetaldehyde 
• 17314-43-1 cyclohex-2-enyltrimethylstannane 
• 64-19-7 acetic acid 
• 1521-51-3 rac-3-bromocyclohexene 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 
• 56666-90-1 9-isopropylidenebicyyclo<6.1.0>nonane 

Downstream Products

• 92-51-3 cyclohexylcyclohexane 

Relevant academic research and scientific papers

Efficient synthesis of 7-, 8- and 9-membered cyclic allyltitanium compounds and their stereoselective addition reaction with aldehydes and imines

Reaction of 7-, 8- and 9-membered cyclic allylic compounds 2 with (η2propene)Ti(O-i-Pr)2 (1) via an oxidative addition pathway provides the corresponding allylic titanium compounds, which, in turn, react with aldehydes and imines stereoselectively, thus providing an efficient and stereoselective method for synthesizing cycloalkenes having a side chain at the allylic position.

Addition of dihalocarbenes to corannulene. A fullerene-type reaction

Dihalocarbenes (:CCl2, :CBr2, and :CI2) add preferentially to one of the radial double bonds of corannulene, rather than to the rim. These cyclopropanations strongly resemble the additions of dihalocarbenes to fullerenes, which likewise occur at 6:6-double bonds, destroy the cyclic conjugation in two adjacent benzene rings, and give 'closed' adducts. An explanation is offered for the abnormally high reactivity of the interior carbon atoms of corannulene. (C) 2000 Elsevier Science Ltd.

The Chemistry of 5-Oxodihydroisoxazoles. XIII. Reactions of the Imino Carbene Derived from Photolysis of Ethyl 5-Oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate

Photolysis of ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate at 300 nm in acetonitrile gives a carbene which is captured efficiently by bromide, chloride, acetate and cyanate, and less efficiently by iodide, thiocyanate, cyclohexene and tetrahydr

Cu-catalyzed asymmetric addition of sp2-hybridized zirconium nucleophiles to racemic allyl bromides

Alkenylzirconium nucleophiles made in situ by the hydrozirconation of terminal alkynes undergo dynamic kinetic asymmetric allylic alkenylation with racemic allyl bromides to give enantioenriched products.

Photochemical Organocatalytic Benzylation of Allylic C–H Bonds

We report a radical-based organocatalytic method for the direct benzylation of allylic C–H bonds. The process uses nonfunctionalized allylic substrates and readily available benzyl radical precursors and is driven by visible light. Crucial was the identification of a dithiophosphoric acid that performs two distinct catalytic roles, sequentially acting as a catalytic donor for the formation of photoactive electron donor–acceptor (EDA) complexes and then as a hydrogen atom abstractor. By mastering these orthogonal radical generation paths, the organic catalyst enables the formation of benzylic and allylic radicals, respectively, to then govern their selective coupling. The protocol was also used to design a three-component radical process, which increased the synthetic potential of the chemistry.

Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids

Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.

Metal-organic framework composites with luminescent pincer platinum(II) complexes: 3MMLCT emission and photoinduced dehydrogenation catalysis

Pincer platinum(ii) complexes are well documented to exhibit weak intermolecular interactions in the solid state and 77 K glassy solutions, leading to emissive triplet metal-metal-to-ligand charge transfer (3MMLCT) excited states that often vanish in dilute solutions. In this work, metal-organic framework (MOF) materials are introduced to provide a "solid solution" environment for easy access to 3MMLCT excited states of pincer platinum(ii) complexes. Phosphorescent composites PtII@MOFs (1-4) with matrix-dependent monomers and oligomer emission properties were obtained. These PtII@MOFs are efficient catalysts for photoinduced dehydrogenation reactions.

Direct cross-coupling between alkenes and tetrahydrofuran with a platinum-loaded titanium oxide photocatalyst

A Pt-loaded TiO2 photocatalyst successfully catalyzed the direct cross-coupling between various alkenes and tetrahydrofuran (THF) without any additional oxidizing agent. The reaction between cyclohexene and THF gave three cross-coupling products, namely, 2-cyclohexyltetrahydrofuran (A), 2-(cyclohex-2-en-1-yl)tetrahydrofuran (B) and 2-(cyclohex-1-en-1-yl)tetrahydrofuran (C), along with gaseous hydrogen. The mechanistic study revealed that these products were formed through different individual mechanisms: successive addition of two radical species, a 2-tetrahydrofuranyl radical and a hydrogen radical, to the double bond of cyclohexene for A, coupling of a 3-cyclohexenyl radical and a 2-tetrahydrofuranyl radical for B, and 2-tetrahydrofuranyl radical addition and hydrogen radical elimination at the double bond of cyclohexene for C. Among these three mechanisms, those for B and C are dehydrogenative. In this photocatalytic reaction system, since the cyclohexene molecule has enough reactivity, due to the localized π electron density, the Pt nanoparticles loaded on the TiO2 function not as a metal catalyst but as an electron receiver to enhance the charge separation, although the dehydrogenative cross-coupling of benzene with THF requires Pd metal catalysis.

Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds

A protocol for the cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds with carboxylic acids was developed in this work. Mechanistic studies revealed that C(sp3)–H bond activation in the hydrocarbon was the turnover-limiting step and the in-situ formed [Co(III)]Ot-Bu did not engage in hydrogen atom abstraction (HAA) of a C–H bond. This protocol was successfully incorporated into a synthetic pathway to β-damascenone that avoided the use of NBS.

Oxidation of aliphatic and aromatic C[sbnd]H bonds by t-BuOOH catalyzed by μ-nitrido diiron phthalocyanine

Low temperature selective transformation of alkanes to useful products continues to be an important challenge in chemistry and industry. μ-Nitrido diiron phthalocyanines in combination with H2O2 have been recently identified as powerful oxidation catalysts for these challenging reactions due to the formation of ultra-high valent diiron oxo species PcFe(IV)μNFe(IV)[dbnd]O(Pc+[rad]). This very strong two-electron oxidizing species is generated from peroxo complex PcFe(IV)μNFe(III)[sbnd]O[sbnd]O[sbnd]R(Pc) (R[dbnd]H in the case of H2O2) via heterolytic O[sbnd]O bond cleavage. Therein we show that the evolution of the peroxo diiron complex depends on the peroxide structure. Using tBuOOH we have demonstrated the formation of an one-electron oxidizing PcFe(IV)μNFe(IV)[dbnd]O(Pc) and tBuO[rad] radical via homolytic O[sbnd]O cleavage of the peroxocomplex. The reactivity of the μ-nitrido diiron tetra-t-butylphthalocyanine ? tBuOOH catalytic system was investigated in the oxidation of different C[sbnd]H bonds in alkanes, olefins, aromatic and alkylaromatic compounds. The main products of cyclohexane oxidation were cyclohexanone and cyclohexanol whereas bicyclohexyl was formed in minor amounts even in the presence of O2 and tBuOOH. Under optimal conditions, the turnover numbers of almost 5300 have been achieved.