Triphenylphosphine oxide supported on non-cross-linked maleimide–styrene copolymer: application as a novel Hendrickson reagent

Mahdavi, Hossein; Amani, Javad

doi:10.1016/j.tetlet.2008.02.001

Cited by 18 publications

(11 citation statements)

References 16 publications

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“…N ‐Benzyl‐4‐nitrobenzamide (3b): R f =0.32 (ethyl acetate/hexane=1:4); white solid; yield: 92% (87 mg, 73%); mp 141–144 °C (lit 28. 142 °C); 1 H NMR (400 MHz, CDCl 3 ): δ =8.26 (d, J =8 Hz, 2 H), 7.94 (d, J =8 Hz, 2 H), 7.37–7.34 (m, 5 H), 6.60 (br s, 1 H), 4.65 (d, J =8 Hz, 2 H); 13 C NMR (100 MHz, CDCl 3 ): δ =165.4, 149.7, 140.0, 137.5, 129.0, 128.3, 128.1, 128.1, 123.9, 44.6; IR (KBr): $\tilde \nu $ =3280 (m), 2922 (m), 2839 (s), 1633 (m), 1597 (m), 1515 (m), 1345 (m), 1105 (s), 870 (s), 697 (s) cm −1 ; HR‐MS (ESI‐TOF): m/z =257.0924, calcd.…”

Section: Methodsmentioning

confidence: 99%

Paramagnetic Relaxation of Long‐Lived Coherences in Solution NMR

et al. 2013

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Long-lived coherences (LLCs) are known to have lifetimes much longer than transverse magnetization or single quantum coherences (SQCs). The effect of paramagnetic ions on the relaxation of LLCs is not known. This is particularly important, as LLCs have potential applications in various fields like analytical NMR, in vivo NMR and MR imaging methods. We study here the behaviour of LLCs in the presence of paramagnetic relaxation agents. The stepwise increase in the concentration of the metal ion is followed by measuring various relaxation rates. The effect of paramagnetic ions is analysed in terms of the external random field's contribution to the relaxation of two coupled protons in 2,3,6-trichlorobenzaldehyde. The LLCs relax faster than ordinary SQCs in the presence of paramagnetic ions of varying character. This is explained on the basis of an increase in the contribution of the external random field to relaxation due to a paramagnetic relaxation mechanism. Comparison is also made with ordinary Zeeman relaxation rates like R1, R2, R1ρ and also with rate of relaxation of long-lived states RLLS which are known to be less sensitive to paramagnetically induced relaxation. Also, the extent of correlation of random fields at two proton sites is studied and is found to be strongly correlated with each other. The obtained correlation constant is found to be independent of the nature of added paramagnetic impurities.

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Section: Methodsmentioning

confidence: 99%

Paramagnetic Relaxation of Long‐Lived Coherences in Solution NMR

et al. 2013

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“…38 Soluble polymeric supports, using a non-cross-linked maleimide-styrene copolymer to which the triphenylphosphine oxide is bound to the maleimide unit, have been investigated. 39 The solubility of this reagent is reported to offer shorter reaction times in comparison to the insoluble polymer-supported reagents, though it is still easily removed from the reaction mixture by precipitation. 39 In addition to solid-supported reagents, cyclic analogs of the Hendrickson reagent have been investigated.…”

Section: First Updatementioning

confidence: 99%

“…39 The solubility of this reagent is reported to offer shorter reaction times in comparison to the insoluble polymer-supported reagents, though it is still easily removed from the reaction mixture by precipitation. 39 In addition to solid-supported reagents, cyclic analogs of the Hendrickson reagent have been investigated. These incorporate two phosphine oxide moieties in a single molecule, linked by an ethylene, a propylene, or a butylene bridge.…”

Section: First Updatementioning

confidence: 99%

Triphenylphosphonium Anhydride Trifluoromethanesulfonate

Hendrickson

Mistry

Moussa

et al. 2014

Encyclopedia of Reagents for Organic Synthesis

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“…For related literature, see: Aghabozorg et al (2007); Aghabozorg et al (2008); Al-Farhan (1992); Chael & Buchmeiser (2003); Mahdavi & Amani (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…3-aminophenyldiphenylphosphine oxide (APDPPO) was prepared from triphenylphosphine oxide according to our previous paper (Mahdavi & Amani, 2008). In this procedure, the solid product was recrystallized from 2-propanol, and 3aminophenyldiphenylphosphine oxide was obtained as white crystals.…”

Section: S2 Experimentalmentioning

confidence: 99%

(3-Aminophenyl)diphenylphosphine oxide–2-propanol (1/1)

Mahdavi

Amani

Gharamaleki³

2008

Acta Cryst E

Self Cite

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The title compound, C18H16NOP·C3H8O, was synthesized by the reduction of (3-nitrophenyl)diphenylphosphine oxide in the presence of 2-propanol as recrystallization solvent. There are two molecules in the asymmetric unit. Each P atom is tetracoordinated by three C and one O atom from two phenyl fragments, one aniline group and one double-bonded O atom in a distorted tetrahedral geometry. C—H⋯π and N—H⋯π interactions are present. In the crystal structure, a wide range of non-covalent interactions consisting of hydrogen bonding [of the types of O—H⋯O, N—H⋯O and C—H⋯O, with D⋯A distances ranging from 2.680 (3) to 3.478 (3) Å] and π–π [centroid–centroid distance of 3.7720 (15) Å] stacking interactions connect the various components into a supramolecular structure.

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Triphenylphosphine oxide supported on non-cross-linked maleimide–styrene copolymer: application as a novel Hendrickson reagent

Cited by 18 publications

References 16 publications

Paramagnetic Relaxation of Long‐Lived Coherences in Solution NMR

Paramagnetic Relaxation of Long‐Lived Coherences in Solution NMR

Triphenylphosphonium Anhydride Trifluoromethanesulfonate

(3-Aminophenyl)diphenylphosphine oxide–2-propanol (1/1)

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