4392-30-7

Usage

InChI:InChI=1/C10H12/c1-2-5-9(6-3-1)10-7-4-8-10/h1-3,5-6,10H,4,7-8H2

Upstream product

• 29681-94-5 3-phenyl-1,4,5,6-tetrahydropyridazine 
• 16547-34-5 2,4-dichloro-3-phenyl-2-cyclobuten-1-one 
• 935-64-8 1-phenyl-1-cyclobutanol 
• 33013-67-1 4,5-epoxy-3-phenyl-hexahydro-pyridazine 
• 3947-97-5 3-phenyl-3-cyclobutene-1,2-dione 
• 100955-66-6 3-phenyl-2-piperidin-1-yl-cyclobut-2-enone 
• 22315-46-4 bromo-phenyl-cyclobutenedione 
• 1198-34-1 2-Phenylcyclopentanone 
• 33013-65-9 4,5-epoxy-3-phenyl-tetrahydro-pyridazine-1,2-dicarboxylic acid diethyl ester 
• 71-43-2 benzene 
• 37828-19-6 1-(phenyl)cyclobutane-1-carboxylic acid 
• 124-41-4 sodium methylate 
• 4399-47-7 Bromocyclobutane 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 7306-05-0 1-methyl-1-phenylcyclobutane 
• 19936-17-5 4-cyclobutylbenzonitrile 
• 3158-70-1 4-cyclobutylbenzoic acid 
• 6921-49-9 4-Nitro-phenyl-cyclobutan 
• 17789-13-8 1-bromo-3-cyclobutylbenzene 
• 19920-94-6 2-Cyclobutyl-nitrobenzol 
• 128309-61-5 4-Cyclobutyl-N,N-dimethyl-benzenesulfonamide 
• 128309-36-4 2-Cyclobutyl-N,N-dimethyl-benzenesulfonamide 
• 128309-50-2 3-Cyclobutyl-N,N-dimethyl-benzenesulfonamide 
• 6921-50-2 1-(4-cyclobutylphenyl)ethenone 
• 100971-56-0 <4-Butyryl-phenyl>-cyclobutan 
• 20211-64-7 cyclobut-2-enyl-benzene 
• 3365-26-2 1-phenylcyclobutene 
• 1170061-50-3 C₁₃H₁₆O 

Relevant academic research and scientific papers

Air-Stable Iron-Based Precatalysts for Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters

The development of an air-stable iron(III)-based precatalyst for the Suzuki-Miyaura cross-coupling reaction of alkyl halides and unactivated aryl boronic esters is reported. Despite benefits to cost and toxicity, the proclivity of iron(II)-based complexes to undergo deactivationviaoxidation or hydrolysis is a limiting factor for their widespread use in cross-coupling reactions compared to palladium-based or nickel-based complexes. The new octahedral iron(III) complex demonstrates long-term stability on the benchtop as assessed by a combination of1H NMR spectroscopy, M?ssbauer spectroscopy, and its sustained catalytic activity after exposure to air. The improved stability of the iron-based catalyst facilitates an improved protocol in which Suzuki-Miyaura cross-coupling reactions of valuable substrates can be assembled without the use of a glovebox and access a diverse scope of products similar to reactions assembled in the glovebox with iron(II)-based catalysts.

Rational Design of an Iron-Based Catalyst for Suzuki–Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles

Suzuki–Miyaura cross-coupling reactions between a variety of alkyl halides and unactivated aryl boronic esters using a rationally designed iron-based catalyst supported by β-diketiminate ligands are described. High catalyst activity resulted in a broad substrate scope that included tertiary alkyl halides and heteroaromatic boronic esters. Mechanistic experiments revealed that the iron-based catalyst benefited from the propensity for β-diketiminate ligands to support low-coordinate and highly reducing iron amide intermediates, which are very efficient for effecting the transmetalation step required for the Suzuki–Miyaura cross-coupling reaction.

Teaching an old carbocation new tricks: Intermolecular C-H insertion reactions of vinyl cations

Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium-weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond-forming reactions, including carbon-hydrogen (C-H) insertion into unactivated sp3 C-H bonds and reductive Friedel-Crafts reactions with arenes. Moreover, we conducted computational studies of these alkane C-H functionalization reactions and discovered that they proceed through nonclassical, ambimodal transition structures. This reaction manifold provides a framework for the catalytic functionalization of hydrocarbons using simple ketone derivatives.

Hydrogenolysis of 1-alkoxybenzocyclobutenes with site-selective cleavage of the sterically hindered C(sp2)-C(sp3) bond

1-Alkoxybenzocyclobutenes undergo ring-opening hydrogenolysis with site-selective cleavage of the sterically hindered C(sp2)-C(sp3) bond on Pd/C.

Nickel-catalyzed reductive cyclization of alkyl dihalides

The reductive coupling protocol to intramolecular cyclization of dihaloalkanes is presented. It leads to five- and six-membered rings, with the former being more efficient. The incorporation of secondary alkyl halides generally promotes coupling efficiency. To the best of our knowledge, this is the first catalytic ring-closure reaction arising from dihaloalkanes under chemical reductive conditions.

Polylithiumorganic compounds. Part 29: C,C Bond cleavage of phenyl substituted and strained carbocycles using lithium metal

The reaction of phenyl substituted cyclopropanes phenylcyclopropane and 1,1-diphenylcyclopropane, phenyl substituted bicyclobutanes 1- phenylbicyclobutane, 1-methyl-3-phenylbicyclobutane, 1-methyl-2,2- diphenylbicyclobutane, as well as phenyl substituted spiropentanes phenylspiropentane and 1,1-diphenylspiropentane with lithium metal or lithium di-t-butylbiphenyl (LiDBB) was investigated. Under suitable reaction conditions and choice of solvent in all cases cleavage of the single bond next to the activating phenyl group was observed. The dilithiumorganic compounds thus obtained are sufficiently stable and can be trapped with electrophiles. Lithium hydride elimination is observed as follow-up reaction only in a few cases. The corresponding anions of the strained ring systems 1-lithio-2,2- diphenylcyclopropane, 1-lithio-3-phenylbicyclobutane, 1-lithio-3-methyl-2,2- diphenylbicyclobutane, and 1-lithio-4-phenylspiropentane, which can be obtained by lithium bromine exchange or by metalation of the unsubstituted carbocycle, do not show any cleavage upon reaction with lithium metal. The reaction of phenyl substituted cyclopropanes, bicyclobutanes as well as spiropentanes with lithium metal with formation of highly reactive dilithiumorganic compounds was investigated. In all cases cleavage of the bond next to the phenyl substituent(s) was observed.

Two-photon generation of the 1,4-diphenyl-1,4-butanediyl biradical: Direct detection and product studies

The 1,4-diphenyl-1,4-butanediyl biradical (3) is generated from 1,4- dichloro-1,4-diphenylbutane (1) or 2,5-diphenylcyclopentanone (8) under several irradiation conditions. The products resulting from this intermediate are styrene (4), 1,2-diphenylcyclobutane (5), and 1-phenyl-1,2,3,4- tetrahydronaphthalene (6). The formation of tetrahydronaphthalenes appears to be a fingerprint for the intermediacy of 1,4-biradicals having a phenyl group attached to one of the radical centers as corroborated in the high-intensity irradiation of 2-phenylcyclopentanone (12). The yield of 6 depends on the substrate and irradiation conditions; this is rationalized as due to a conformational memory effect of the nascent biradical.

Side Chain Hydroxylation of Aromatic Compounds by Fungi. Part 5. Exploring the Benzylic Hydroxylase of Mortierella isabellina

The active site topography of the hydroxylase enzyme of Mortierella isabellina ATCC 42613, which carries out the benzylic hydroxylation of toluene, ethylbenzene, and related compounds, has been explored.Operating in a whole cell biotransformation mode, this enzyme shows selectivity in substrate processing based on the nature, position and size of substituent side chains close to the site of hydroxylation.The results of determination of the yield and stereochemistry of hydroxylation of over twenty substrates and potential substrates, together with previously reported data, have been used to propose an active site model for the benzylic hydroxylase enzyme.

Pyrolysis of 9-Methylenespironona-5,7-diene: A Route to Benzo-2-hexene-1,6-diyl, a Putative Intermediate in the Retro-Diels-Alder Reaction of Tetralin

A precursor to the 1,6-biradical potentially formed in the retro-Diels-Alder reaction of tetralin, namely, 5-methylenespirohept-2-ene-6,1'-cyclobutan>-7-one (9) has been prepared and found to give tetralin and o-allyltoluene upon pyrolysis in solution below 100 deg C and upon flash vacuum pyrolysis around 250 deg C.The product ratio changes from 1:1 to 6:1 at higher temperatures.Rate-determining loss of CO from 9 to give 9-methylenespironona-5,7-diene, 2, has been demonstrated by trapping the triene with N-methyl- and N-phenyltriazolinedione in a reaction whose rate is independent of trapping agent concentration.The kinetics for loss of ketone, 9, gave log k (s-1) = 14.628 +/- 0.038 - (30.554 +/- 0.064)/2.3RT.Pyrolysis of cis-syn(to methylene)- and trans-1,2-dimethyl-9-methylenespironona-5,7-diene gives the vinylcyclobutane rearrangement product, 2,3-dimethyltetralin, with a 4:1 and 2.7:1, respectively, preference for retention over inversion at the migrating carbon.Hydrogen shift products are also formed and by highly ordered transiton states.One of these hydrogen shifts involves an unprecedented shift from the carbon remote from the vinyl group.