Michaelis-Arbuzov rearrangement

Bhattacharya, Alok K.; Thyagarajan, G.

doi:10.1021/cr00044a004

Cited by 810 publications

(424 citation statements)

References 37 publications

Supporting

Mentioning

417

Contrasting

Unclassified

Order By: Relevance

“…Table 5 Photopolymerization reactivity, photopolymerization time, operation time, flexural strength and flexural modulus, and color tone of experimental, visible-light curing dental resin composites 65.8%. After obtaining CQ-APO through the Michaelis-Arbuzov reaction 9,10) at Step 3, the νC=O absorption band (1776.44 cm -1 ) of CQ-COCl disappeared but the νC=O absorption band (1749.44 cm -1 ) of acylphosphine oxide group was recorded in the FT-IR spectrum, thus, the pale yellow crystal obtained could be identified as CQ-APO. Figure 6 shows a schematic illustration of the mechanism of Michaelis-Arbuzov reaction 9,10) , which is frequently used in organophoshorus chemistry 10,13) , between methoxydiphenylphosphine (MDPP) [CH3O-P(Ph)2] and CQ-COCl to yield CQ-APO and methyl chloride.…”

Section: Synthesis Of Cq-apo a Photoinitiator Having Both α-Diketone mentioning

confidence: 99%

Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance

et al. 2010

View full text Add to dashboard Cite

Camphorquinone (CQ) derivatives having acylphosphine oxide (APO) group are unknown. This study synthesized such a novel 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carbonyldiphenyl phosphine oxide (DOHC-DPPO = CQ-APO). Ultraviolet and visible (UV-VIS) spectra of CQ-APO, CQ, and APO were measured. Photopolymerization performances of experimental light-cured resins comprising these photoinitiators were investigated. Newly synthesized CQ-APO showed as a pale yellow crystal (mp 365K). UV-VIS spectrum of CQ-APO showed two maximum absorption wavelengths (λmax) [372 nm (from APO group) and 475 nm (from CQ moiety)] within 350-500 nm. Unfilled resin containing CQ-APO exhibited good photopolymerization time (9.6 sec) and relaxed operation time (50 sec), as well as a pronouncedly lower b value (4.0) in the CIELab color specification system than that containing CQ (84.0). Resin composites containing CQ-APO, exhibited high flexural strength . It was concluded that CQ-APO possessed two λmax peaks within 350-500 nm, and that CQ-APO-containing resins exhibited excellent color tone, good photopolymerization reactivity, relaxed operation time, and high mechanical strength.

show abstract

Section: Synthesis Of Cq-apo a Photoinitiator Having Both α-Diketone mentioning

confidence: 99%

Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance

et al. 2010

View full text Add to dashboard Cite

show abstract

“…1. 2,4,6-trimethylbenzoyl-methoxy-phenylphosphine oxide(TMMPO) Title compound was synthesized by MichaelisArbuzov reaction 13,14) of 2,4,6-trimethylbenzoyl chloride (TMC) (16.7 g, 91.2 mmol) with dimethoxyphenyl phosphine (DMPP) (17.0 g, 100 mmol) in dry toluene (130 ml) for 5 hours at 60°C. After the reaction,thesolventwasremovedandalightyellow viscousliquidofTMMPOwasobtained(17.8g,75.0% yield).…”

Section: Synthesis Of Apo-namentioning

confidence: 99%

Design of a new dental adhesive-Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

et al. 2009

View full text Add to dashboard Cite

Thebehaviorofwater-solublephotoinitiatorswithcrownethersindentaladhesivesisunknown.Thisstudyinvestigatedthe effectofsodiumacylphosphineoxide(APO-Na)withcrownetherinahydrophobicadhesiveonadhesiontoteeth.Sodium 2,4,6-trimethylbenzoyl-phenylphosphine oxide (TMPO-Na = APO-Na) was synthesized in 67.1% yield and identified by 1 H NMR. APO-Na was dissolved in hydrophobic resins in the presence of a crown ether (ionophore effect). Thirty kinds of experimentalsingle-stepadhesivescomprisingAPO-Na,CE,Bis-GMA,6-methacryloyloxyhexylphosphonoacetate(6-MHPA), and4-methacryloyloxyethyltrimelliticacid(4-MET)weretherebyprepared.Shearbondstrengthtounetchedgroundteeth wasmeasuredatacrossheadspeedof1.0mm/min,andthedatawereanalyzedbyANOVA.Theshearbondstrengthresults of bonding resins containing APO-Na with 18-crown-6-ether (CE-6) were significantly higher than that without CE-6 (control) (p<0.05).Higherbondstrengthvalues[forenamel:BR24at19.3(3.2)MPa;fordentin:BR29at20.2(4.7)MPa]wereachieved with the adhesives containing APO-Na, CE-6, 6-MHPA, and 4-MET. Therefore, it was found that APO-Na with CE-6 contributed to the efficient bonding performance of single-step adhesive to teeth. However, in view of the biosafety hazard posedbycrownethers,thesearchisstillonforreagentsthatarebiologicallysaferthancrownethers-butwithionophor effects-tobeusedindentaladhesives.

show abstract

“…During reaction the trivalent phosphorous was converted into the pentavalent one. It has been reported [32] that the conversion of the >P-O-C linkage into >P(=O)-C involves a net gain of 32 kcal/mol energy in the total bond stability which acts as a driving force for the rearrangement. The synthesis of shorter chain lengths was difficult due to high reactivity and most of the time resulted in a polymer insoluble in common organic solvents.…”

Section: Synthesismentioning

confidence: 99%

Novel Modified Pyrrole Monomers, 1: Synthesis and Characterization

Oberoi

Jähne

Adler

et al. 2008

Designed Monomers and Polymers

View full text Add to dashboard Cite

Different 1-substituted-(pyrrole alkyl)phosphonic acid derivatives have been designed as adhesion promoters to graft polypyrrole layers on several substrates. These compounds contain two reactive, terminal moieties: the phosphonic acid group as anchor to the oxide surface and the pyrrolyl group, which functions as starting unit for surface polymerisation. Both groups are connected by an alkyl spacer ranging from 4 to 12 methylene units. The short-and long-chain derivatives were synthesized for the first time to study their self-assembling properties and their effectiveness to be used as an adhesion promoter for grafting covalently bound polypyrrole layers on oxide substrates. Surfactant-like properties of the long chain derivatives and their behaviour in water for pyrrole polymerization were also investigated, as will be discussed in future papers. In this first paper of the series, the synthesis and characterization of the monomers are presented. The structure of the molecules was proven by 1 H-NMR, 31 P-NMR and FT-IR spectroscopy. Thermogravimetry analysis (TGA) and differential scanning calorimetry (DSC) revealed that the stability of the compound depended on their chain length: the longer the alkyl chain, the more stable the monomer. On the other hand, reactivity decreased with increasing chain length, as proven by cyclic voltammetry measurements (CV).  Koninklijke Brill NV, Leiden, 2008

show abstract

Michaelis-Arbuzov rearrangement

Cited by 810 publications

References 37 publications

Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance

Synthesis of a novel camphorquinone derivative having acylphosphine oxide group, characterization by UV-VIS spectroscopy and evaluation of photopolymerization performance

Design of a new dental adhesive-Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

Novel Modified Pyrrole Monomers, 1: Synthesis and Characterization

Contact Info

Product

Resources

About