Category: 4141-48-4

Eren, Nimrod M. published the artcileSynthesis, Structure, and Solution Studies of Lithiated Allylic Phosphines and Phosphine Oxides, Safety of Allyldiphenylphosphine oxide, the publication is Organometallics (2020), 39(11), 2080-2090, database is CAplus.

This study reports a new series of 12 ¦Á-lithiated allylic phosphines and phosphine oxides. By incorporating Lewis base donors including di-Et ether (Et₂O), THF (THF), N,N,N’,N’,-tetramethylethylenediamine (TMEDA), and N,N,N’,N’,N”,-pentamethyldiethylenetriamine (PMDETA), nine complexes were structurally characterized by single-crystal X-ray crystallog. This includes novel dilithiated allylic phosphine 4 [PhP{CHCHCH₂Li(TMEDA)}₂] and a rare hemisolvated lithiated phosphine oxide 6 [{Ph₂P(O)CHC(Me)CH₂Li}₂(TMEDA)]. Interestingly, in the solid state, P(III) complexes take advantage of Li-¦Ð interactions to the newly formed delocalized system, in comparison to P(V) complexes where the oxophillic nature of the lithium atom dominates. All 12 complexes were fully characterized in the solution state by multinuclear NMR spectroscopy. DFT calculations on isomers of monomeric lithiated complex 3 [Ph₂PCHC(Me)CH₂Li(PMDETA)] described the low energy barrier between transition steps of the subtle delocalization of the allylic chain.

Organometallics published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Safety of Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Toyota, Masahiro published the artcileAn expeditious and efficient formal synthesis of (¡À)-aphidicolin, Application In Synthesis of 4141-48-4, the publication is Tetrahedron Letters (1994), 35(35), 6495-8, database is CAplus.

An expeditious and efficient formal total synthesis of antiviral and antitumor tetracyclic diterpene aphidicolin has been developed. An intramol. Heck reaction and an intramol. Diels-Alder reaction were utilized as key steps in the sequence.

Tetrahedron Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C9H8BNO2, Application In Synthesis of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Toyota, Masahiro published the artcileEnantioselective total synthetic route to (+)-aphidicolin, Application In Synthesis of 4141-48-4, the publication is Tetrahedron Letters (1995), 36(30), 5379-82, database is CAplus.

Enantioselective total synthetic route to (+)-aphidicolin has been described. Cycloisomerization reaction of I to give II and intramol. Diels-Alder reaction of III to give IV were employed for the key steps of the sequence.

Tetrahedron Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C4H12ClNO, Application In Synthesis of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Toyota, Masahiro published the artcileSynthesis of a cancer growth-inhibiting diterpene – stereoselective formal synthesis of (+)-aphidicolin, Product Details of C15H15OP, the publication is Tetrahedron (1996), 52(31), 10347-10362, database is CAplus.

Stereoselective formal synthesis of the diterpene tetraol (+)-aphidicolin is described, employing as key steps the cycloisomerization of the enyne I to provide the bicyclo[3.2.1]octane derivative II and the intramol. Diels-Alder reaction of the triene III to form the aphidicolane-type ring system. This route is, in principal, highly stereocontrolled and extremely efficient.

Tetrahedron published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C9H12BNO4, Product Details of C15H15OP.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nishimura, Takahiro published the artcilePalladium-Catalyzed Transformation of Cyclobutanone O-Benzoyloximes to Nitriles via C-C Bond Cleavage, Computed Properties of 4141-48-4, the publication is Journal of Organic Chemistry (2004), 69(16), 5342-5347, database is CAplus and MEDLINE.

Pd-catalyzed transformation of cyclobutanone O-benzoyloximes to a variety of nitriles is described. The reaction may proceed via two important steps, i.e., (i) oxidative addition of the N-O bond of oximes to Pd(0) to give a cyclobutylideneaminopalladium(II) species and (ii) ¦Â-C elimination of this species to afford a reactive alkylpalladium species. The kind of products is very dependent on the nature of substituents on the cyclobutane ring. The direction of the C-C bond cleavage is controlled by the kind of ligand employed. For example, (Z)-2-Allyl-3,3-dibenzylcyclobutanone O-benzoyloxime gave 19/81 and 78/22 2,2-Dibenzyl-4-methylenecyclopentanecarbonitrile and (E)-3,3-Dibenzylhepta-4,6-dienenitrile when two different chiral ligands were used. The sequential reaction composed of the C-C bond cleavage and the subsequent intra- and intermol. C-C bond formations via the corresponding alkylpalladium species is also demonstrated. For example, an oxime having an alkynyl moiety at a suitable position reacts with a variety of alkenes to afford nitriles bearing dienylcyclopentane moiety in moderate to good yields. For example, 50 % [3-[(E,E)-4-(diphenylphosphinyl)-1-phenylbut-2-enylidene]-1-methylcyclopentyl]acetonitrile (characterized by x-ray crystallog.) was obtained from 3-methyl-3-(4-phenylbut-3-ynyl)cyclobutanone O-benzoyloxime and Ph₂P(O)CH₂CH:CH2 in DMF in the presence of K₂CO₃, Pd(dba)₂ and (R)-BINAP.

Journal of Organic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Computed Properties of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Takacs, James M. published the artcileCatalytic iron-mediated ene carbocyclizations: formal [4+4]-ene reactions of triene esters, Formula: C15H15OP, the publication is Tetrahedron (1990), 46(16), 5507-22, database is CAplus.

2-Substituted 2,7,9-decatrienoates, e.g., I, undergo an iron-catalyzed carbocyclization to yield trans-disubstituted cyclopentanes, e.g., II, in moderate-to-good chem. yields. The cyclization products are formally the result of a [4+4]-ene reaction in which cis-propenyl and 2-acryloyl functionalities are introduced as appendages to the newly formed cyclopentane ring by the cyclization. Triene ester substrates bearing an alkyl substituent at the 4- or 6-positions cyclize with high 1,2-stereoinduction to yield trisubstituted cyclopentanes in which the relative stereochem. between three contiguous stereocenters is controlled.

Tetrahedron published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H19NO5, Formula: C15H15OP.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Takacs, James M. published the artcileCatalytic iron-mediated triene carbocyclizations: stereoselective five-membered ring forming carbocyclizations, Name: Allyldiphenylphosphine oxide, the publication is Journal of Organic Chemistry (1994), 59(23), 6928-42, database is CAplus.

The full details of studies into the regiochem. and stereochem. of Fe-catalyzed carbocyclizations of 2,7,9-decatriene derivatives to form five-membered carbocyclic ring systems are described. The sense and degree of simple diastereoselection depends upon the (2E/2Z)-alkene geometry. In general, (2E,7E)-trienes are the preferred substrate and give rise to 5-membered ring products in which the 2 newly ring formed substituents have the cis relative stereochem. E.g., treating triene I under the standard reaction conditions (dropwise addition of 3.1 equiv Et₃Al to a cooled (0-5¡ã) solution of triene, 10-20 mol. % Fe(acac)₃ and an equivalent amount of 2,2′-bipyridine in 10 mL C₆H₆ or preferably PhMe) gave > 80% cyclopentane derivative II. The roles of the allylic substituent, the alkene geometry, diene substitution, and the influence of resident stereogenic centers incorporated in the tether chain connecting the reacting 1,3-diene and alkene subunits are discussed.

Journal of Organic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Name: Allyldiphenylphosphine oxide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Takacs, James M. published the artcileCatalytic iron-mediated ene carbocyclizations of trienes: enantioselective synthesis of the iridoid monoterpenes (-)-mitsugashiwalactone and (+)-isoiridomyrmecin, SDS of cas: 4141-48-4, the publication is Tetrahedron Letters (1992), 33(3), 317-20, database is CAplus.

The iron-catalyzed cycloisomerization of a chiral (2E,7E)-2,7,9-decatriene derivative e.g. I containing an Me substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident Me-containing stereocenter. The stereochem. of the chiral cyclopentane product II is proven by conversion to (-)-mitsugashiwalactone (III) and to (+)-isoiridomyrmecin (IV).

Tetrahedron Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C14H14N2O2, SDS of cas: 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Runge, M. Brett published the artcileNew selectivities from old catalysts. Occlusion of Grubbs’ catalysts in PDMS to change their reactions, Synthetic Route of 4141-48-4, the publication is Journal of Organometallic Chemistry (2006), 691(24-25), 5278-5288, database is CAplus.

This article describes new selectivities for Grubbs’ first and second generation catalysts when occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS). Occlusion of catalysts in mm-sized slabs of PDMS is accomplished by swelling with methylene chloride then removing the solvent under vacuum. The catalysts are homogeneously dissolved in PDMS yet remain catalytically active. Many substrates that react by olefin metathesis with Grubbs’ catalysts freely dissolved in methylene chloride also react by olefin isomerization with occluded catalysts. Eleven examples of substrates that exhibit dual reactivity by undergoing olefin isomerization with occluded catalysts and olefin metathesis with catalysts dissolved in methylene chloride are reported. Most of these substrates have olefins with allylic phosphine oxides, carbonyls, or ethers. Control experiments demonstrate that isomerization is occurring in the solvent by decomposition of the catalyst from a ruthenium carbene to a proposed ruthenium hydride. This work was extended by heating occluded Grubbs’ first generation catalyst to 100¡ã in 90% MeOH in H₂O in the presence of various alkenes to transform the Grubbs’ catalyst into an isomerization catalyst for unfunctionalized olefins. This work demonstrates that occlusion of organometallic catalysts in PDMS has important implications for their reactions and can be used as a method to control which reactions they catalyze.

Journal of Organometallic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Synthetic Route of 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Goldberg, Daniel R. published the artcileThe tandem intramolecular Diels-Alder reaction, SDS of cas: 4141-48-4, the publication is Tetrahedron Letters (1993), 34(50), 8003-6, database is CAplus.

The tandem intramol. Diels-Alder (TIMDA) reaction of ketone I is reported to give tetracyclic ketone II. The reaction proceeds under mild conditions (BF₃¡¤Et₂O, 0¡ãC) and affords two tetracyclic products diastereoselectively. TIMDA substrate I is prepared in a convergent manner from 1,5-pentanediol.

Tetrahedron Letters published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, SDS of cas: 4141-48-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia