Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

Adamczyk, Maciej; Watt, David S.; Netzel, Daniel A.

doi:10.1021/jo00196a024

Cited by 89 publications

(65 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[32] The EI spectrum of 12a is consistent with the EI mass spectrum of 1-propyl-3H-indene. [33] The reaction of 2-heptyne with the complexes 3a and 3b, respectively, lead to products corresponding to the ones with 2-hexyne. The EI spectra of the β-hydride elimination products ( Figure 6) thereof are in accordance with the β- hydride elimination products of 2-hexyne, just shifted by one CH 2 unit.…”

Section: Reaction Of Complexes 3a and 3b With Alkynes Leads To The Fomentioning

confidence: 99%

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

et al. 2010

View full text Add to dashboard Cite

Square planar arenido-(triphenylphosphane)nickel(II) complexes (3) containing a N,O-chelate ligand are catalysts for the carbon monoxide/ethene copolymerisation reaction. Pathways for catalyst deactivation have been elucidated by investigating the reactions of such complexes with aliphatic unsaturated compounds like olefins and alkynes. We have shown that the double or triple bond, respectively, inserts into the nickel-carbon bond followed by β-hydride elimination resulting in aryl-substituted olefins and allenes, which

show abstract

Section: Reaction Of Complexes 3a and 3b With Alkynes Leads To The Fomentioning

confidence: 99%

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

et al. 2010

View full text Add to dashboard Cite

show abstract

“…Gas chromatography/mass spectrometry (GC-MS) was performed by electronic impact at 70 eV. 1-Bromo-2-(but-3-enyl)benzene (1) [33,109] [35] 4-bromo-3-(bromomethyl)-phenyl methyl ether (7b), [110] authentic samples of but-3-enylbenzene (1l) [33] and 1-methylindane (1c) [33,111] were prepared as described in literature. The reaction between bromide 1 and Mg has been described previously.…”

Section: Methodsmentioning

confidence: 99%

Structural Effects in Radical Clocks and Mechanisms of Grignard Reagent Formation: Special Effect of a Phenyl Substituent in a Radical Clock when the Crossroads of Selectivity is at a Metal/Solution Interface

et al. 2009

View full text Add to dashboard Cite

A large class of radical clocks is based on the intramolecular trapping of a reactive radical by a suitably located unsaturated system. Depending on the substituents present on this unsaturated system, the rate of cyclisation may vary drastically. This property has been repeatedly used to diagnose the participation of very short-lived radicals in the mechanisms of a wide variety of reactions. For reactions occurring in homogeneous solution, a phenyl substituent capable of stabilizing the radical formed during the act of trapping has been one of the most widely used tools of this type. During study of the mechanisms of formation of Grignard reagents -reactions that occur at the interface of the metal and the solution -the phenyl substituent displayed a specific new behaviour pattern. Besides its stabilizing role, it was also able to play the role of mediator in redox catalysis of electron transfer. In this case, the first events on the pathway to the Grignard reagents involve a cascade of three (one intermolecular followed by two intramolecular) electron transfers. Introduction of a p-methoxy substituent on the phenyl ring, making the phenyl group a poorer electron acceptor, suppresses this

show abstract

“…[5b] 1-bromo-1-cyclopentene (5a), [20] 1-bromo-1-cyclohexene (5b), [20] 5-bromo-3,4-dihydro-2H-pyran (5c), [20] 3-bromo-1,2-dihydronaphthalene (5e), [21] 2-bromo-6-methoxy-3,4-dihydro-2H-naphthalen-1-one, [22] 2-bromo-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol, [21] (-)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one, [23] 1-ethynyl-1-cyclopentene (6a), [24] 2-methyl-1-buten-3-yne (6h), [24] 1-ethynyl-1-cyclohexene (6b), [24] 1-buten-3-yne (6i), [24] 2,5-dimethyl-1,5-hexadien-3-yne (2hh), [25] pentacarbonyl [18] were prepared according to published procedures.…”

Section: Generalmentioning

confidence: 99%

Cascade Reactions of β‐Amino‐Substituted α,β‐Unsaturated Fischer Carbene Complexes with 1,5‐Dien‐3‐ynes as a Convenient Access to Ring‐Annelated Benzene Derivatives

Wu¹,

Noltemeyer²,

Meijere³

2005

Eur J Org Chem

View full text Add to dashboard Cite

Upon heating pentacarbonyl(3-dimethylamino-1-ethoxypropenylidene)chromium complexes 1 with 1,5-dien-3-ynes 2 in pyridine at 80°C, benzene-annelated cyclopentenones 8 and their regioisomers 9, resulting from a sequence of cocyclization, 6π-electrocyclization and hydrolysis, were isolated in 12-75 % yield (13 examples). The more flexible the alkenyl substituents were in the dienynes 2, the longer were the reaction times needed to achieve good chemical yields. This new cascade reaction of Fischer carbene complexes provides

show abstract

Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

Cited by 89 publications

References 1 publication

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

Structural Effects in Radical Clocks and Mechanisms of Grignard Reagent Formation: Special Effect of a Phenyl Substituent in a Radical Clock when the Crossroads of Selectivity is at a Metal/Solution Interface

Cascade Reactions of β‐Amino‐Substituted α,β‐Unsaturated Fischer Carbene Complexes with 1,5‐Dien‐3‐ynes as a Convenient Access to Ring‐Annelated Benzene Derivatives

Contact Info

Product

Resources

About