37689-22-8

Upstream product

• 96-40-2 2-cyclopenten-1-yl chloride 
• 118-92-3 anthranilic acid 
• 142-29-0 cyclopentene 
• 20657-21-0 3-acetoxycyclopent-1-ene 
• 28557-00-8 phenylzinc chloride 
• 16958-34-2 (Z)-1-cyclopropyl-2-phenyl ethylene 
• 16958-35-3 (E)-1-cyclopropyl-2-phenyl ehtylene 
• 542-92-7 cyclopenta-1,3-diene 
• 62-53-3 aniline 
• 64-19-7 acetic acid 
• 36367-82-5 trans-2-phenylcyclopentyl p-bromobenzenesulfonate 
• 591-50-4 iodobenzene 
• 114895-10-2 phenylazoxy phenyl sulphone 
• 100-34-5 benzene diazonium chloride 

Downstream Products

• 20383-31-7 1,2-epoxy-3-phenyl-cyclopentane 
• 106055-34-9 di(3-phenyl-2-cyclopentenyl) peroxide 
• 90046-72-3 diethyl 2-hydroxy-2-(1-phenylcyclopenten-3-yl)propane-1,3-dioate 
• 74755-35-4 1-bromo-2-phenyl-cyclopentane 
• 101999-42-2 (+/-)-2-phenyl-1,5-pentanediol 
• 3810-26-2 3-phenyl-2-cyclopenten-1-one 

Relevant academic research and scientific papers

Photochemical and chemical electron transfer reactions of bicyclo[2.1.0]pentanes (housanes) in solution and in zeolite cavities

Photochemical electron transfer (PET) and chemical electron transfer (CET) studies have been conducted in solution and within zeolite cavities for the bicyclo[2.1.0]pentanes (2a-j), prepared by direct photolysis of the corresponding azoalkanes 1. The adva

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.

Dinuclear Pathways for the Activation of Strained Three-Membered Rings

Dinuclear, strain-induced ring-opening reactions of vinylaziridines and vinylcyclopropanes are described. The previously reported [NDI]Ni2(C6H6) complex (NDI = naphthyridine-diimine) reacts with N-tosyl-2-vinylaziridine via C-N oxidative addition to generate a dinickel metallacyclic product. On the basis of this stoichiometric reactivity, the [NDI]Ni2(C6H6) complex is shown to be a highly active catalyst for the rearrangement of vinylcyclopropane to cyclopentene. Notably, 2-phenyl-1-vinylcyclopropane undergoes regioselective activation at the less hindered C-C bond in contrast to the noncatalytic thermal rearrangement. DFT calculations provide insight into the ability of the Ni-Ni bond to stabilize key intermediates and transition states along the catalytic pathway.

Cycloalkyl-based unsymmetrical unsaturated (U2)-NHC ligands: Flexibility and dissymmetry in ruthenium-catalysed olefin metathesis

Air-stable Ru-indenylidene and Hoveyda-type complexes bearing new unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands combining a mesityl unit and a flexible cycloalkyl moiety as N-substituents were synthesised. Structural features, chemical stabilities and catalytic profiles in olefin metathesis of this new library of cycloalkyl-based U2-NHC Ru complexes were studied and compared with their unsymmetrical saturated NHC-Ru homologues as well as a set of commercially available Ru-catalysts bearing either symmetrical SIMes or IMes NHC ligands.

Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions

An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

Alder-ene reaction of aryne with olefins

A novel intermolecular Alder-ene reaction based on aryne and olefins was developed. We performed this transformation under mild conditions such as at room temperature, and this reaction displayed high selectivity and good yields only in the presence of CsF. Hence, the intermolecular Alder-ene reaction of aryne with olefins provides an effective route to synthesize derivatives of olefins.

Enantioselective synthesis of chiral sulfones by ir-catalyzed asymmetric hydrogenation: A facile approach to the preparation of chiral allylic and homoallylic compounds

A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Baecklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).

BINAP versus BINAP(O) in asymmetric intermolecular Mizoroki-Heck reactions: Substantial effects on selectivities

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was employed as chiral ligand in the enantioselective intermolecular Mizoroki-Heck reaction, whereas the use of cognate BINAP(O) (monooxidized BINAP) is unprecedented. The regio- and enantioselectivity of the arylation of representative cyclic alkenes changes dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The arylation of 2,3-dihydrofuran is perfectly regiodivergent (98:2 versus 0:100) and the arylation of cyclopentene is only enantioselective with BINAP(O) [60 versus 10% enantiomeric excess (ee)]. Use of [Pd2(dba)3]·dba (dba=dibenzylideneacetone) instead of Pd(OAc)2 produces as high as 86% ee in the arylation of cyclopentene.

Mild two-step process for the transition-metal-free synthesis of carbon-carbon bonds from allylic alcohols/ethers and grignard reagents

Chemical Equation Represented A mild two-step process for the regioselective, transition-metal-free preparation of carbon-carbon bonds from allylic alcohols/ethers and Grignard reagents is described. This process obviates the need for the harsh deprotecti

Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement

(Chemical Equation Presented) A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane- cyclopentene rearrangement