ChemInform Abstract: Recent Developments in Phosphasilene Chemistry

Winkel, Y. Van Den; Bastiaans, H. M. M.; Bickelhaupt, F.

doi:10.1002/chin.199045378

Cited by 4 publications

(4 citation statements)

References 1 publication

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“…All starting materials were obtained from commercial suppliers and used without further purification. Ferrocenylphosphine,66 2,4,6‐mesitylphosphine,67 2,4,6‐tri‐ tert ‐butylphenylphosphine,68 (2,4,6‐tri‐ tert ‐phenyl)phenylphosphine,69 2 ,70 and 3 a 50 were prepared according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Influence of P‐Bonded Bulky Substituents on Electronic Interactions in Ferrocenyl‐Substituted Phospholes

Miesel

Hildebrandt

Korb

et al. 2015

Chemistry A European J

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2,5-Diferrocenyl-1-Ar-1H-phospholes 3 a-e (Ar=phenyl (a), ferrocenyl (b), mesityl (c), 2,4,6-triphenylphenyl (d), and 2,4,6-tri-tert-butylphenyl (e)) have been prepared by reactions of ArPH2 (1 a-e) with 1,4-diferrocenyl butadiyne. Compounds 3 b-e have been structurally characterized by single-crystal XRD analysis. Application of the sterically demanding 2,4,6-tri-tert-butylphenyl group led to an increased flattening of the pyramidal phosphorus environment. The ferrocenyl units could be oxidized separately, with redox separations of 265 (3 b), 295 (3 c), 340 (3 d), and 315 mV (3 e) in [NnBu4 ][B(C6 F5 )4]; these values indicate substantial thermodynamic stability of the mixed-valence radical cations. Monocationic [3 b](+)-[3 e](+) show intervalence charge-transfer absorptions between 4650 and 5050 cm(-1) of moderate intensity and half-height bandwidth. Compounds 3 c-e with bulky, electron-rich substituents reveal a significant increase in electronic interactions compared with less demanding groups in 3 a and 3 b.

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Section: Methodsmentioning

confidence: 99%

Influence of P‐Bonded Bulky Substituents on Electronic Interactions in Ferrocenyl‐Substituted Phospholes

Miesel

Hildebrandt

Korb

et al. 2015

Chemistry A European J

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“…NMR spectra: Avance DRX 400 (Bruker), standards: 1 H NMR (400 MHz): internal solvent, 13 [50,51], and [PtCl 2 (cod)] [52,53] were prepared according to literature procedures. NMR spectra: Avance DRX 400 (Bruker), standards: 1 H NMR (400 MHz): internal solvent, 13 [50,51], and [PtCl 2 (cod)] [52,53] were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, structure, and transition metal complexes of amphiphilic 1,5‐diaza‐3,7‐diphosphacyclooctanes

Карасик

Naumov

Balueva

et al. 2006

Heteroatom Chemistry

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“…Styrene was purchased from Aldrich and distilled from CaH 2 prior to use. L ‐Valinol,27 oxazoline 4 ,26 MesP(SiMe 3 ) 2 ,19 2,4,6‐( i Pr) 3 C 6 H 2 P(SiMe 3 ) 2 ,37 2‐ i PrC 6 H 4 P(SiMe 3 ) 2 ,33 and 2‐ t BuC 6 H 4 P(SiMe 3 ) 2 33 were prepared according to literature procedures. 1 H, 31 P{ 1 H}, and 13 C{ 1 H} NMR spectra were recorded at 25 °C on Bruker Avance 300 or 400 MHz spectrometers.…”

Section: Methodsmentioning

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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ChemInform Abstract: Recent Developments in Phosphasilene Chemistry

Cited by 4 publications

References 1 publication

Influence of P‐Bonded Bulky Substituents on Electronic Interactions in Ferrocenyl‐Substituted Phospholes

Influence of P‐Bonded Bulky Substituents on Electronic Interactions in Ferrocenyl‐Substituted Phospholes

Synthesis, structure, and transition metal complexes of amphiphilic 1,5‐diaza‐3,7‐diphosphacyclooctanes

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

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