Category: 4141-48-4

Lautens, Mark published the artcileCobalt-Catalyzed [2¦Ð + 2¦Ð + 2¦Ð] (Homo-Diels-Alder) and [2¦Ð + 2¦Ð + 4¦Ð] Cycloadditions of Bicyclo[2.2.1]hepta-2,5-dienes, HPLC of Formula: 4141-48-4, the publication is Journal of the American Chemical Society (1995), 117(26), 6863-79, database is CAplus.

The scope of the cobalt-catalyzed [2¦Ð + 2¦Ð + 2¦Ð] (homo-Diels-Alder, HDA) and [2¦Ð + 2¦Ð + 4¦Ð] cycloaddition reactions with norbornadienes has been investigated. Cobalt acetylacetonate, Co(acac)₃ or Co(acac)₂, upon reduction by diethylaluminum chloride (Et₂AlCl) in the presence of 1,2-bis(diphenylphosphino)ethane (dppe), is very effective in promoting the HDA reaction between norbornadiene and a variety of unactivated acetylenes to yield deltacyclenes. Azeotropic drying of the cobalt compound before use is found to increase the reactivity of the catalyst. Moderate to excellent enantioselectivity of these [2¦Ð + 2¦Ð + 2¦Ð] (up to 91% ee) and [2¦Ð + 2¦Ð + 4¦Ð] (up to 79% ee) cycloadditions can be achieved by the use of a chiral phosphine. 7-Substituted norbornadienes are also found to be reactive in the cobalt-catalyzed HDA reactions, affording the corresponding deltacyclenes in good yields. However, low anti/syn selectivities are observed, in contrast with the corresponding nickel-catalyzed HDA reaction with electron-deficient dienophiles. 2-Substituted norbornadienes are found to be less reactive in the cobalt-catalyzed HDA reactions, and the regio- and stereoselectivities are only moderate. The intramol. versions of these [2¦Ð + 2¦Ð + 2¦Ð] and [2¦Ð + 2¦Ð + 4¦Ð] cycloadditions have also been investigated and provide efficient methods for the construction of highly strained pentacyclic frameworks from norbornadiene.

Journal of the American Chemical Society 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, HPLC of Formula: 4141-48-4.

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

Nicolaou, K. C. published the artcileIodine(V) Reagents in Organic Synthesis. Part 2. Access to Complex Molecular Architectures via Dess-Martin Periodinane-Generated o-Imidoquinones, Application of Allyldiphenylphosphine oxide, the publication is Journal of the American Chemical Society (2002), 124(10), 2221-2232, database is CAplus and MEDLINE.

2-Amido-1,4-benzoquinones can be prepared from 4-substituted anilides lacking pendant alkenes by treatment with DMP and water followed by careful workup under neutral conditions. The oxidative preparation of 2-amido-1,4-benzoquinones has been used in the synthesis of the natural products epoxyquinomycin B and BE-10988 and in the preparation of a macrocyclic amide with a tetrahydronaphthoquinone moiety. Ortho-substituted N-aryl acetamides lacking pendant alkenes undergo oxidation with DMP and water to give o-imidoquinones which are stable for several months when stored under argon at low temperature in the absence of light. O-imidoquinones undergo intermol. Diels-Alder cycloadditions with vinyl ethers and sulfides to give phenoxazines. The treatment of anilides containing pendant alkenes with Dess-Martin periodinane (DMP) in the presence of water gives oxazine-containing polycyclic compounds by stereoselective oxidation to o-imidoquinones followed by stereoselective intramol. Diels-Alder cycloaddition The isobutyrylaminophenylheptadiene (E)-Me₂CHCONH-4-C₆H₄CH₂CH₂CH₂CH:CHCH:CH₂ undergoes stereoselective oxidative cyclization upon treatment with DMP in methylene chloride to give ketoamidohydroxyphenalenone I in 28% yield and an amidoquinone which undergoes thermal Diels-Alder cyclization to give hexahydrobenzindene II in 25% yield; I and II are related to the natural products pseudopterosin A and elisabethin A, resp. The ketohydroxyamide moiety in I undergoes cyclization, condensation, and cyclocondensation reactions with aromatic amines, aromatic diamines, amino acid esters, and amino alcs. to give spirocycles, fused diazaheterocycles, and phenalene derivatives

Journal of the American Chemical Society 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, Application of Allyldiphenylphosphine oxide.

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

Nicolaou, K. C. published the artcileNew synthetic technology for the construction of N-containing quinones and derivatives thereof: total synthesis of epoxyquinomycin B, COA of Formula: C15H15OP, the publication is Angewandte Chemie, International Edition (2001), 40(1), 207-210, database is CAplus and MEDLINE.

N-substituted p-quinones and o-azaquinones are prepared regioselectively in a one-step tandem double oxidation of anilides by Dess-Martin periodinane. This process is applied to the short and efficient total synthesis of epoxyquinomycin B. The intermol. and intramol. Diels-Alder reactions of N-containing quinones are demonstrated. The o-azaquinones are shown to participate in inverse electron demand Diels-Alder reactions with electron-rich olefins.

Angewandte Chemie, International Edition 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, COA of Formula: C15H15OP.

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

Wlodarczyk, Katarzyna published the artcileIntramolecular cationic cyclization of ¦Â-hydroxyalkylphosphine oxides-a route towards the benzophosphorinane core, Safety of Allyldiphenylphosphine oxide, the publication is Tetrahedron (2016), 72(33), 5074-5090, database is CAplus.

Intramol. cationic cyclization of ¦Â-hydroxyalkylphosphine oxides in the presence of an acid gives fused bicyclic compounds with an incorporated P atom. Depending on the structure of the starting compound the formation of either phosphaindane or benzophosphorinane oxides was observed The key difference in the reactivity arises from the substitution pattern at the carbinolic C atom of ¦Â-hydroxyalkylphosphine oxide.

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 C7H5Br2F, Safety of Allyldiphenylphosphine oxide.

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

Ishii, Keitaro published the artcilePhotoreactions of ¦Â-aziridinylacrylonitriles and acrylates with alkenes: the substituent effects on the formation of [3+2] cycloadducts, SDS of cas: 4141-48-4, the publication is Tetrahedron (2006), 62(47), 10865-10878, database is CAplus.

The photochem. C,C-bond cleavage of trisubstituted aziridines I (R¹ = H, PhCH₂; R² = Me, Ph; R³ = H; R⁴ = CN, EtO₂C) followed by [3 + 2] cycloaddition with electron-deficient alkenes, such as tert-Bu acrylate, afforded the novel head-to-head adducts, 1,2,3,5-tetrasubstituted pyrrolidines, e.g. II, selectively and efficiently. The aziridine (cis,Z)-I (R¹ = PhCH₂; R² = Me; R³ = H; R⁴ = CN) reacted with mol. oxygen affording dioxazolidine III, whereas (trans,E)-I (R¹ = PhCH₂; R² = Ph; R³ = H; R⁴ = EtO₂C) produced only cleaved products. The results may suggest that the C,C-bond of aziridine cleaves biradically. The photoreactions of N-tritylaziridines I (R¹ = Ph₃C; R² = H; R³ = R⁴ = MeO₂C, CN; R³ = H, R⁴ = H₂C:CH) possessing diester, dinitrile, and butadiene groups in the side chain with electron-deficient alkenes, such as vinyl acetate or acrylonitrile, yielded 2,3-cis-pyrrolidines IV exclusively. In particular, the dinitrile I (R¹ = Ph₃C; R² = H; R³ = R⁴ = CN) also reacted with non-electron-deficient alkenes, such as isoprene. The formal synthesis of the indolizidine fragment of stellettamides starting from the pyrrolidine (E)-IV (R³ = H; R⁴ = H₂C:CH; R⁵ = CN) was achieved in a convenient manner.

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 C15H15OP, SDS of cas: 4141-48-4.

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

Yamamoto, Hirofumi published the artcileHg(OTf)₂-catalyzed cycloisomerization of aryl- and hetero-substituted 1,3-dienes, Recommanded Product: Allyldiphenylphosphine oxide, the publication is Chemistry Letters (2010), 39(8), 830-831, database is CAplus.

The authors developed Hg(OTf)₂-catalyzed Friedel-Crafts-like cycloisomerization of 7-arylhepta-1,3-dienes to give propenyl-substituted tetrahydronaphthalenes in excellent catalytic turnover under very mild conditions. 1,3-Dienyl sulfonamides and 1,3-dienyl alcs. were also efficiently cyclized to afford heterocyclic compounds

Chemistry 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 C14H12N2S, Recommanded Product: Allyldiphenylphosphine oxide.

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

Toyota, Masahiro published the artcileSynthetic approach to stemodin (I) – a novel stereocontrolled construction of the stemodane system by the successive intramolecular Diels-Alder reactions, Application In Synthesis of 4141-48-4, the publication is Tetrahedron (1994), 50(4), 1093-104, database is CAplus.

The synthesis of the A, B, C and D ring part I of the diterpene stemodin (II) from 1,4-cyclohexanedione monoethylene ketal III by use of successive intramol. Diels-Alder reactions is described.

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 C6H12F3NO5S, Application In Synthesis of 4141-48-4.

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

Toyota, Masahiro published the artcileSynthetic approach to stemodin – a novel stereocontrolled construction of the stemodane system by successive intramolecular Diels-Alder reactions., Name: Allyldiphenylphosphine oxide, the publication is Tetrahedron Letters (1992), 33(32), 4581-4, database is CAplus.

The tetracyclic compound I, possessing the stemodane skeleton, was synthesized from 1,4-cyclohexanedione monoethylene ketal. The key steps involve intramol. Diels-Alder reactions, namely ketone II to tricycle III and triene IV to I.

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 C11H8ClN3, Name: Allyldiphenylphosphine oxide.

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

Feldmann, Kai-Oliver published the artcileA versatile protocol for the quantitative and smooth conversion of phosphane oxides into synthetically useful pyrazolylphosphonium salts, HPLC of Formula: 4141-48-4, the publication is ChemSusChem (2011), 4(12), 1805-1812, database is CAplus and MEDLINE.

A convenient protocol for the smooth conversion of the resistant P:O bond in phosphane oxides R₂R¹P:O into a reactive P-N bond of synthetically useful pyrazolylphosphonium salts is described. A highly charged, oxophilic, phosphorus-centered trication [P₂(¦Ì-3,5-Me₂Pz)₃][OTf]₃ (1, 3,5-Me₂Pz = 3,5-dimethyl-1-pyrazolyl-N,N’) is employed as a deoxygenating reagent, and the reactions are conducted at room temperature with quant. yields. The resulting pyrazolylphosphonium cations [R₂R¹P(3,5-Me₂Pz)][OTf] (3a–g, R = Ph, Et, Bu; R₂ = CH:CMeCH₂CH₂; R¹ = Ph, Me, Et, CH₂CH:CH₂) are valuable synthetic intermediates and are used for the synthesis of a variety of organophosphorus compounds Protonation of 3a facilitates P-N-bond cleavage and reduction or substitution reactions. Triphenylphosphine may be obtained by electrochem. or LiAlH₄ reduction of 3a. Alkylation of 3a with BuLi gave the phosphonium ylide, Ph₃P:CHPr, which was used in Wittig olefination of 2-nitrobenzaldehyde. This represents a new approach towards the transformation of the rather inert phosphoryl group under very mild reaction and workup conditions and aims towards alternatives to existing reduction methods for phosphane oxide functionalization.

ChemSusChem 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, HPLC of Formula: 4141-48-4.

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

Liu, Rong Qiang published the artcile2-Alkenyldiphenylphosphine oxides and PO-ylides derived thereof in trans selective Horner-Wittig olefination reactions, COA of Formula: C15H15OP, the publication is Synlett (1996), 1195-1196, database is CAplus.

Allylic PO-ylides generated by deprotonation of 2-alkenyldiphenylphosphine oxides with BuLi were used to prepare 1,3-dienes trans-selectively. The (Z/E) ratios of the newly formed double bond are 1:99 when straight-chain, while they were 2:98 to 4:96 when ¦Â-branched aliphatic, and 4:96 to 6:94 when aromatic aldehydes were employed.

Synlett 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, COA of Formula: C15H15OP.

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