133886-27-8

Basic information

• Product Name: (-)-(3aR,4S,7R,7aR)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one
• CAS NO: 133886-27-8
• Molecular Weight: 222.287
• Mol File: 133886-27-8.mol

Chemical Properties

• CAS DataBase Reference: (-)-(3aR,4S,7R,7aR)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(3aR,4S,7R,7aR)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one(133886-27-8)
• EPA Substance Registry System: (-)-(3aR,4S,7R,7aR)-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoinden-1-one(133886-27-8)

Safety Data

• Hazardous Substances Data: 133886-27-8(Hazardous Substances Data)

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1224969-70-3 dicobalttetracarbonyl(μ-phenylacetylene)(μ2-P,S-N-benzyl-trifluoromethylsulfinamide) 
• 15226-74-1 dicobalt octacarbonyl 
• 536-74-3 phenylacetylene 
• 123-73-9 crotonaldehyde 
• 201230-82-2 carbon monoxide 

Relevant articles and documents

Rate Enhancement of the Pauson-Khand Reaction by Primary Amines

Keywords: alkyne complexes; amines; carbonyl complexes; cobalt; cyclization

Heterobimetallic (Co-W) intermolecular Pauson-Khand reactions: Scope and selectivity

Heterobimetallic μ-alkyne complexes [η5-Cp(CO)2W(μ-R1C2R 2)Co(CO)3] are suitable substrates for the intermolecular Pauson-Khand reaction. They can be obtained in higher yields than the corresponding Mo-Co complexes, and the reaction with norbornadiene of those derived from several 2-butynoates offers a convenient way to the preparation of endo-fused, 1,3-dicarbonyl cyclopentenone adducts.

Synthesis of highly functionalized pentalenes via intermolecular Pauson-Khand reaction

A concise synthetic route to highly substituted pentalenones 4 and 5, respectively, is reported. The key step is a Pauson-Khand reaction of norbornadiene (7) with the functionalized acetylenes 8 to give the methanoindenone derivatives 6. 1,4-Addition of o

Catalytic Pauson-Khand Reaction in Ethylene Glycol-Toluene: Activity, Selectivity, and Catalyst Recycling

The use of ethylene glycol (15% v/v in toluene) as additive in the catalytic Pauson-Khand reaction (PKR) is reported. In most cases both the yield and selectivity were enhanced compared to standard protocols. Moreover, the immiscibility of ethylene glycol

Asymmetric intermolecular cobalt-catalyzed pauson-khand reaction using a p-stereogenic bis-phosphane

The asymmetric intermolecular and catalytic Pauson-Khand reaction has remained an elusive goal since Khand and Pauson discovered this transformation. Using a novel family of P-stereogenic phosphanes, we developed the first catalytic system with useful lev

Nitrous Oxide Promoted Pauson-Khand Cycloadditions

A Pauson-Khand cycloaddition of alkynes, alkenes, and carbon monoxide promoted by cobalt carbonyl and nitrous oxide to furnish cyclopentenones is described. Preliminary mechanistic experiments suggest that nitrous oxide functions in a manner similar to th

PNSO ligands as a tool to study metal bonding of electron-deficient sulfinyl groups

A family of N-phosphanylsulfinamide (PNSO) ligands with electron-deficient sulfinyl groups was synthesized. Reaction with Co2-alkyne complexes yields P,S-bridged complexes. These complexes were used to study the metal bonding of different sulfinyl groups. IR spectroscopy, X-ray analysis, and Pauson-Khand reactivity studies indicated that electron-deficient sulfinyl groups provide enhanced S metal bonding. The mean CO stretching frequencies (Δv) for these complexes closely correlates with the χi parameter computed by Tolman for phosphane ligands. Among the studied sulfinyl groups, the trifluoromethyl PNSO ligand afforded the strongest sulfur-metal bond. Wiley-VCH Verlag GmbH & Co. KGaA.

Dicobaltbisnorbornadienetetracarbonyl [Co2(nbd) 2(CO)4] reacts with oxygen-containing alkynes and gives crossover products in the presence of other alkenes

Dicobaltbisnorbornadienetetracarbonyl, [Co2(nbd) 2(CO)4] DDTC, (nbd = norbornadiene) which has previously been reported to be unreactive with alkynes is shown to react with oxygen-containing alkynes; in the presence of oth

Immobilized Co/Rh heterobimetallic nanoparticle-catalyzed Pauson-Khand-type reaction

Co/Rh heterobimetallic nanoparticles were prepared from cobalt-rhodium carbonyl clusters [Co2Rh2(CO)12 and Co 3Rh(CO)12] and immobilized on charcoal. HR-TEM revealed that the size of the heterobimetal

Intermolecular cobalt-mediated Pauson-Khand reactions in ionic liquids

Intermolecular Pauson-Khand reactions of strained alkenes 1a-d with alkynes 2, 4, 6 and Co2(CO)8 were performed in [bmim]PF6 either thermally or in the presence of NMO. For comparison thermal reactions were done in toluene and NMO-promoted reactions in CH2Cl2. The results show that the ionic liquid is a suitable substitute for CH2Cl2. Yields of the NMO-promoted reaction could be improved by using a two-phase system [bmim]PF6/methylcyclohexane.