2,4,6‐Tri‐<i>tert</i>‐butylphenyl and 2,4‐di‐<i>tert</i>‐butyl‐6‐methylphenyl groups: Look similar, react differently

Ionkin, Alex S.; Marshall, William J.

doi:10.1002/hc.10083

Cited by 32 publications

(23 citation statements)

References 17 publications

(16 reference statements)

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“…This is in marked contrast to the only other uncomplexed pyridylbisphosphaalkene which has been structurally characterized, i.e. II (Scheme 1), in which the PC units are twisted by as much as 63° [8]. This significant twisting limits the electronic interaction between the PC units and the central aromatic ring so that no conjugation can be expected for II .…”

Section: Resultsmentioning

confidence: 83%

Synthesis, structure and π-delocalization of a phosphaalkenyl based neutral PNP-pincer

Orthaber¹,

Belaj²,

Pietschnig³

2011

Inorganica Chimica Acta

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Graphical abstractA novel bis-phosphaalkenyl based PNP-pincer was prepared and its crystal structure indicates delocalization over the entire π-system including all three donor sites which is also supported by spectroscopic measurements and DFT calculations. The coordination chemistry of the pincer and its precursor have been explored using Cu(I).Highlights► A novel bis-phosphaalkenyl based PNP-pincer was prepared. ► The crystal structure indicates delocalization over the entire π-system including all three donor sites. ► DFT calculations and UV–Vis measurements support the interpretation of the structural findings. ► The coordination behavior towards Cu(I) is explored on a preliminary base.

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Section: Resultsmentioning

confidence: 83%

Synthesis, structure and π-delocalization of a phosphaalkenyl based neutral PNP-pincer

Orthaber¹,

Belaj²,

Pietschnig³

2011

Inorganica Chimica Acta

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“…The crude product was recrystallized from n-pentane to afford colorless crystals of 1 a (52 %), which were characterized crystallographically. The optical activity of the product was confirmed by polarimetry and the Flack parameter [0.13 (9)], determined crystallo- graphically, suggested that the S configuration of 1 a was assigned correctly. Moreover, all of the compounds leading to phosphaalkene 1 a were similarly optically active.…”

Section: Resultsmentioning

confidence: 99%

“…

CHPh} y ] n (9 a: x = 0.13n, y = 0.87n; GPC: M w = 7400 g mol À1 , PDI = 1.15).(1,3)-butadiene B, [7] phosphinidene-imine C, [8] and 2,6-bis-(phosphaethenyl)pyridine D. [9] These ligands incorporate the bulky Mes* substituent, and the effects of this large group on mechanistic processes relevant to catalysis (ligand exchange, substrate binding, turnover, etc.) are not well understood.

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confidence: 99%

Enantiomerically Pure Phosphaalkene–Oxazolines (PhAk‐Ox): Synthesis, Scope and Copolymerization with Styrene

Dugal-Tessier

Serin

Castillo-Contreras

et al. 2012

Chemistry A European J

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The design of a synthetic route to a class of enantiomerically pure phosphaalkene-oxazolines (PhAk-Ox) is presented. The condensation of a lithium silylphosphide and a ketone (the phospha-Peterson reaction) was used as the P=C bond-forming step. Attempted condensation of PhC(=O)Ox (Ox = CNOCH(iPr)CH(2)) and MesP(SiMe(3))Li gave the unusual heterocycle (MesP)(2)C(Ph)=CN-(S)-CH(iPr)CH(2)O (3). However, PhAk-Ox (S,E)-MesP=C(Ph)CMe(2)Ox (1 a) was successfully prepared by treating MesP(SiMe(3))Li with PhC(=O)CMe(2)Ox (52 %). To demonstrate the modularity and tunability of the phospha-Peterson synthesis several other phosphaalkene-oxazolines were prepared in an analogous manner to 1 a: TripP=C(Ph)CMe(2)Ox (1 b; Trip = 2,4,6-triisopropylphenyl), 2-iPrC(6)H(4)P=C(Ph)CMe(2)Ox (1 c), 2-tBuC(6)H(4)P=C(Ph)CMe(2)Ox (1 d), MesP=C(4-MeOC(6)H(4))CMe(2)Ox (1 e), MesP=C(Ph)C(CH(2))(4)Ox (1 f), and MesP=C(3,5-(CF(3))(2)C(6)H(3))C(CH(2))(4)Ox (1 g). To evaluate the PhAk-Ox compounds as prospective precursors to chiral phosphine polymers, monomer 1 a and styrene were subjected to radical-initiated copolymerization conditions to afford [{MesPC(Ph)(CMe(2)Ox)}(x){CH(2)CHPh}(y)](n) (9 a: x = 0.13n, y = 0.87n; GPC: M(w) = 7400 g mol(-1) , PDI = 1.15).

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“…A further 31 structures proved to have questionable values for density or a dubious structure as identified in the CSD or by using the CheckCIF online program and 27 structures could not be evaluated because of insufficient data (i.e., no available cif). The following structures satisfy the search criteria and are potential candidates for purely organic microporous crystals: ABINOP, [31] BALNIM, [24] EFALEC, [32] FAKTIV, [33] GIPTOO, [34] KETYEO, [35] NASQAA, [36] PETREM, [37] RERNEI, [38] SULDUY [39] TOZZIR, [40] WAVJAE, [41] XICRUW, [42] XOPYEG, [43] and YUPTIM. [44] In addition, the following metal-containing structures are candidates as microporous molecular crystals: ADIYIV, [45] FOSTEM, [46] FOSTEM10, [47] GOBSUL, [47] IKANOX, [48] KISYIV, [49] PICKAN, [50] and TIKFIC.…”

Section: Methodsmentioning

confidence: 99%

Nitrogen and Hydrogen Adsorption by an Organic Microporous Crystal

et al. 2009

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Aufnahmefähig: Die außergewöhliche Kristallstruktur von 3,3′,4,4′‐Tetra(trimethylsilylethinyl)biphenyl wurde untersucht. Durch Entfernen eingeschlossener Solvensmoleküle entsteht ein organischer Kristall mit einer weitmaschigen mikroporösen Struktur, die derjenigen von Zeolith A verblüffend ähnlich ist (siehe Bild). Experimente zur reversiblen Adsorption von Stickstoff oder Wasserstoff bei 77 K bestätigten, dass die Mikroporen permanent bestehen bleiben.magnified image

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2,4,6‐Tri‐tert‐butylphenyl and 2,4‐di‐tert‐butyl‐6‐methylphenyl groups: Look similar, react differently

Cited by 32 publications

References 17 publications

Synthesis, structure and π-delocalization of a phosphaalkenyl based neutral PNP-pincer

Synthesis, structure and π-delocalization of a phosphaalkenyl based neutral PNP-pincer

Enantiomerically Pure Phosphaalkene–Oxazolines (PhAk‐Ox): Synthesis, Scope and Copolymerization with Styrene

Nitrogen and Hydrogen Adsorption by an Organic Microporous Crystal

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