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Journal articles on the topic 'Phosphorous ylide'

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Published: 3 June 2025

Last updated: 31 July 2025

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1

Endrich, K., P. Alburquerque, R. P. Korswagen, and M. L. Ziegler. "Über die Reaktionen von Phosphoryliden mit homodinuklearen Organometallverbindungen des Molybdän und Wolfram / On the Reaction of Phosphorylides with Homodinuclear Organometallic Compounds of Molybdenum and Tungsten." Zeitschrift für Naturforschung B 43, no. 10 (1988): 1293–306. http://dx.doi.org/10.1515/znb-1988-1015.

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We report first the complete study of the reactions of [CpMo(CO)2]2 (Mo≡Mo) (1, Cp = η5-C5H5) with salt-free phosphorus ylides Ph3P=CHR (2, Ph = C6H5; R = H (2a), CH3 (2b), C3H7 (2c), C6H5 (2d)) and with the Nal-adducts of the ylides Ph3P=CMe2 (Me = CH3), PhMe2P=CH2 and (PhO)3P=CH2. With 2, products of the type Cp(CO)2LMo-MoL(CO)2Cp (7, L = ylide) were obtained, and the salt adducts gave addition compounds of the type Cp(CO)2LMo-MoL(CO)2Cp-2NaI (12, L = ylide). These very reactive products represent novel bisphosphonioalkyl complexes, and were characterized by IR, mass and 1H NMR spectrometry.

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2

Ilia, Gheorghe, Vasile Simulescu, Nicoleta Plesu, Vlad Chiriac, and Petru Merghes. "Wittig and Wittig–Horner Reactions under Sonication Conditions." Molecules 28, no. 4 (2023): 1958. http://dx.doi.org/10.3390/molecules28041958.

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Carbonyl olefinations are among the most important organic syntheses that form C=C bonds, as they usually have high yields and in addition offer excellent stereoselectivity. Due to these advantages, carbonyl olefinations have important pharmaceutical and industrial applications. These reactions contain an additional step of an α-functionalized carbanion to an aldehyde or ketone to produce alkenes, but syntheses performed using metal carbene complexes are also known. The Wittig reaction is an example of carbonyl olefination, one of the best ways to synthesize alkenes. This involves the chemical

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3

Melgarejo, Doris Y., Gina M. Chiarella, Ahmed A. Mohamed, and John P. Fackler. "An Octanuclear Gold(I) Cube with Amidinate Ligands Containing Two Hyper-coordinate Ylide Carbon Atoms." Zeitschrift für Naturforschung B 64, no. 11-12 (2009): 1487–90. http://dx.doi.org/10.1515/znb-2009-11-1232.

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Disparate properties of gold(I) converge to produce the first known cube assembly of eight Au(I) atoms connected by four N-bridging amidinate ligands on the sides of the cube, capped above and below by hyper-coordinate carbon atoms from a phosphorous ylide. There are no phosphines coordinated to the Au(I) atoms. The cluster is formulated as [Au8{CH(NC8H9)2}4{(η5- C)P(C6H5)2(CH3)}2]. It displays a strong green luminescence under UV light. The novel product was generated in an attempt to produce luminescent species of gold(I) with mixed C- and Ncoordination, an arrangement not abundant in the li

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4

Erker, Gerhard, Peter Czisch, and Richard Mynott. "Die Bildung eines Zirconium-substituierten Phosphor-Ylids durch sigmatrope Wasserstoffverschiebung / Formation o f a Zirconium Substituted Phosphorus Ylide by Sigmatropic Hydrogen Migration." Zeitschrift für Naturforschung B 40, no. 9 (1985): 1177–80. http://dx.doi.org/10.1515/znb-1985-0914.

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σ-Crotylmetallocenyl substituted ylides (1) Cp2M(-CH2CH=CHCH3)(CHPPh3), M=Zr,Hf, are formed upon treatment of a mixture of (s-cis-) and (s-trans-η4-butadiene)metallocene complexes with the phosphorus ylide methylenetriphenylphosphorane (4). From the ( s-cis-/s-trans-butadiene) zirconocene equilibrium mixture (7/5) only the (s-cis-conjugated diene)metallocene isomer reacts with the ylide at -50 °C. Under kinetic control the fram-σ-crotylzirconocenyl-ylide (lb) is formed selectively; subsequent crotyl cis-trans-isomerization (1b⇆1b′) takes place at higher temperature (> -20 °C ). A mechanism

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5

Al-Bashir, Rasha F., Nouria A. Al-Awadi, and Osman ME El-Dusouqui. "Synthesis of novel sulfonyl-stabilized phosphorus ylides, and the kinetics and mechanism of their conventional and flash vacuum pyrolysis reactions." Canadian Journal of Chemistry 83, no. 9 (2005): 1543–53. http://dx.doi.org/10.1139/v05-210.

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Nine substituted sulfonyl-stabilized phosphorus ylides were prepared by treating their intermediate ylide analogues with phenylmethanesulfonyl fluoride. The stoichiometric ratio of the reactants for each preparation needed to be adjusted according to the basicity of each ylide intermediate. The nine ylide compounds were then subjected to conventional (sealed-tube) gas-phase pyrolysis at 470545 K. The pyrolytic reactions were homogeneous and obeyed a first-order rate equation. The values of the Arrhenius log A (s1) and Ea (kJ mol1) obtained for these reactions averaged 11.12 ± 2.00 and 131.8

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6

Habibi-Khorassani, Sayyed Mostafa, Malek Taher Maghsoodlou, Ali Ebrahimi, et al. "Theoretical study and synthesis of the reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and 2-aminobenzimidazole, 2-hydroxy-3-nitropyridine or 1,2,3,4-tetrahydrocarbazole." Collection of Czechoslovak Chemical Communications 75, no. 8 (2010): 785–805. http://dx.doi.org/10.1135/cccc2009523.

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Triphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of heterocyclic compounds, such as 2-aminobenzimidazole, 2-hydroxy-3-nitropyridine or 1,2,3,4-tetrahydrocarbazole to generate stable phosphorus ylides. Some ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon–carbon partical double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group, whereas others occur as a single isomer only. For this reason, the assignments of more stable Z- or E-isomers as the major or minor forms

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7

Sun, Xiu-Li, Jun-Cheng Zheng, and Yong Tang. "Iron carbenoid-mediated ylide reactions." Pure and Applied Chemistry 82, no. 3 (2010): 625–34. http://dx.doi.org/10.1351/pac-con-09-10-20.

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Electrophilic metal carbenoids, readily available from diazo compounds, prove to be good reagents for the preparation of ylides under neutral conditions. We have extended the strategy to synthesize allenes from diazoacetates with both stable and unstable ketenes in the presence of PPh3 and Fe(TCP)Cl (0.5 mol %), which provided an easy access to optically active 4,4-disubstituted allenic esters by employing enantiopure phosphines. The mechanism involving the generation of ylide through catalytic transfer of an iron(II) carbene to phosphine was confirmed. A tandem Wittig–Nazarov cyclization reac

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8

Maghsoodlou, Malek Taher, Norollah Hazeri, Sayyed Mostafa Habibi Khorasani, Ghafar Afshari, and Mahmoud Nassiri. "A facile synthesis of stable heterocyclic fused ring phosphorus ylides." Journal of Chemical Research 2005, no. 11 (2005): 727–28. http://dx.doi.org/10.3184/030823405774909478.

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Stable crystalline phosphorus ylides were obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates, and strong NH-acids, such as 7-azaindole. These stabilised phosphoranes exist as a mixture of two geometrical isomers as a result of restricted rotation around the carbon–carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.

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9

Ramazani, Ali, Ali Reza Kazemizadeh, Ebrahim Ahmadi, Katarzyna Ślepokura, and Tadeusz Lis. "Synthesis and X-Ray Single Crystal Structure of Dialkyl 2-[1-(2,2-Dimethylpropionyl)-3,3-dimethyl-2-oxobutyl]-3- (triphenylphosphoranylidene)succinates." Zeitschrift für Naturforschung B 61, no. 9 (2006): 1128–33. http://dx.doi.org/10.1515/znb-2006-0911.

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Abstract A one-pot synthesis of sterically congested phosphorus ylides in fairly high yields by the reaction of 2,2,6,6-tetramethyl-3,5-heptanedione, dialkyl acetylenedicarboxylates and triphenylphosphine is reported. The structures of these compounds were confirmed by IR, 1H, 31P and 13C NMR spectroscopy, and X-ray single crystal structure determination. The NMR spectra (CDCl3 as solvent) indicated that the compounds contained two rotamers for each ylide.

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10

Sabounchei, Seyyed Javad, Mojdeh Sadat Hashemi, Ali Hashemi, et al. "Pd/Pt metallacyclopropa[60]fullerene complexes bearing versatile phosphorous ylide ligands; a comprehensive multi-spectroscopic, electrochemistry, theoretical and catalytic studies." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 204 (November 2018): 416–24. http://dx.doi.org/10.1016/j.saa.2018.06.079.

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11

Karami, Kazem, Zahra Shirani-Sarmazeh, Mahboubeh Hosseini-Kharat, Janusz Lipkowski, and Maryam Saeidifar. "Synthesis, spectral characterization, crystal structure and in vitro DNA/protein binding studies of phosphorous ylide palladacyclic complexes containing azide group." Journal of Photochemistry and Photobiology B: Biology 144 (March 2015): 11–19. http://dx.doi.org/10.1016/j.jphotobiol.2015.01.012.

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12

Karsch, Hans H., Roland Richter, and Annette Schier. "Tetra-heteroelementsubstituierte Methane und isomere Phosphorylide: C- versus P-Nucleophilie ambidenter Phosphinomethanide / Tetra-Heteroelement Substituted Methanes and Isomeric Phosphorus Ylides: C- versus P-Nucleophilicity of Ambidentate Phosphinomethanides." Zeitschrift für Naturforschung B 48, no. 11 (1993): 1533–43. http://dx.doi.org/10.1515/znb-1993-1111.

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Fully heteroelement substituted carbanions, i.e. phosphinomethanides of the type [(Me2P)C(X)(Y)]- (X, Y = PMe2, SiMe3) react with organoelement chlorides (X—Cl, Y—Cl) to give tetra-heteroelement substituted methanes and/or isomeric phosphorus ylides with an element-phosphorus bond. The latter in some cases are rigid, in others fluctional and in certain cases may rearrange to the isomeric methane derivatives. The results are explained by the involvement of pentacoordinated silicon derivatives, which only occur as transient species, however. A compound with pentacoordinated silicon in the ground

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13

Breton, Gary W. "The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course." Journal of Chemical Education 74, no. 1 (1997): 114. http://dx.doi.org/10.1021/ed074p114.

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14

Kayser, Margaret M., and Livain Breau. "On the regioselectivity of Wittig reactions with unsymmetrically substituted succinic anhydrides." Canadian Journal of Chemistry 67, no. 9 (1989): 1401–10. http://dx.doi.org/10.1139/v89-215.

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Phosphorane ylids react readily with succinic anhydrides to give enol-lactones. With highly substituted succinic anhydrides, condensations occur at the less substituted carbonyl group, suggesting that the reaction is sterically controlled. This, however, is not the case in monosubstituted anhydrides where effects other than steric become dominant. Condensation of phosphorane 1a with methoxysuccinic anhydride occurs selectively at the carbonyl group adjacent to the substituent. Stabilization of the transition state through complexation between the oxygen atom of the substituent and an electron-

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15

Kavounis, C. A., A. P. Bozopoulos, and C. J. Cheer. "A phosphorous ylide with a secondary P…O bond. The crystal structure of a-[6-furazano][3,4-b]-quinoxalinyl-a-carbethoxymethylenetriphenylphosphorane(butene-2,3,4-dimethylhexene-3)solvate." Zeitschrift für Kristallographie 188, no. 3-4 (1989): 299–306. http://dx.doi.org/10.1524/zkri.1989.188.3-4.299.

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16

Sedghi, Asieh, Seyyed Javad Sabounchei, Abed Yousefi, Mohsen Sayadi, Mehdi Bayat, and Robert W. Gable. "C, C coordination mode in comparison with C, P coordination mode in six and seven pallada- and platinacycle complexes of phosphorous ylide; synthesis, X-ray and theoretical studies." Journal of Molecular Structure 1214 (August 2020): 128216. http://dx.doi.org/10.1016/j.molstruc.2020.128216.

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17

Sandblom, Nicole, Tom Ziegler, and Tristram Chivers. "A density functional study of the bonding in tertiary phosphine chalcogenides and related molecules." Canadian Journal of Chemistry 74, no. 11 (1996): 2363–71. http://dx.doi.org/10.1139/v96-263.

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The nature of the phosphorus–tellurium bond in tertiary phosphine tellurides is not well understood. There is also controversy over the nature of multiple bonding in the lighter chalcogenides and the related ylides and imides. Density functional theory (DFT) was used to investigate the interactions in the molecule, Me3PE (E = O, S, Se, Te, BH3, CH2, NH). The calculated PE bond energies and orbital populations reveal contributions from both σ donation from the phosphine and π back-donation to the phosphine in all of the above cases. Down the group from oxygen to tellurium, the PE bond weakens f

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18

Aghdaei, Elham, Sayyed Mostafa Habibi-Khorassani, and Mehdi Shahraki. "Variable temperatures 1H NMR technique on the kinetics and thermodynamic parameters of equilibrium between the Z and E isomers in a stable phosphorus ylide involving an imidazole." RSC Advances 6, no. 52 (2016): 46345–49. http://dx.doi.org/10.1039/c6ra09758h.

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Analysis of <sup>1</sup>H NMR spectra of a special ylide involving an imidazole at variable temperatures has been employed to study the kinetics of the interchangeable process in the equilibrium between the two Z- and E-isomers of a stable phosphorus ylide.

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19

Weber, Lothar, Dietmar Wewers, and Ewald Lücke. "Übergangsmetallkomplexe instabiler Ylide, IX [1] Zur Reaktivität von Pentacarbonyl(dimethyloxosulfoniomethanid)chrom(0) gegenüber Organoelementmethyldiphenylphosphanen RnECH2PPh2 (ERn = Ph2Sb, MeS, PhS, PhSe) und (RnE)2CH2 (RnE = Ph2Sb, MeS)." Zeitschrift für Naturforschung B 40, no. 7 (1985): 968–74. http://dx.doi.org/10.1515/znb-1985-0720.

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Abstract Treatment of the sulfur ylide complex (CO)5Cr[CH2S(O)Me2] (1) with the bifunctional phosphines Ph2PCH2ERn (ERn = SMe, SPh, SePh) lead to pentacarbonylchromium phosphorus ylide complexes (CO)5CrCH2PPh2CH2ERn. Only the S-methyl derivate could be converted to the metallocycle (CO)4[xxx] (ERn = SMe) by UV-irridiation. The ylide chelate complex (CO)4[xxx]Ph2 is formed directly by the thermal reaction of Ph2PCH2SbPh2 with 1. N o ylide complexes result from the reaction of 1 with (Ph2Sb)2CH2 and (MeS)2CH2. The only products identified were (CO)5Cr[Ph2SbCH2SbPh2] and [(CO)5CrS(Me) - ]2CH2, re

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20

Habibi-Khorassani, Sayyed Mostafa, Malek Taher Maghsoodlou, Ali Ebrahimi, Fatemeh Vasheghani Farahani, Elahe Mosaddeg, and Mohammad Amin Kazemian. "Dynamic 1H NMR study around the heteroaryl–carbon and carbon–carbon single bonds and also around carbon–carbon double bond in a particular phosphorous ylide involving a 2-methyl indole." Tetrahedron Letters 50, no. 26 (2009): 3621–24. http://dx.doi.org/10.1016/j.tetlet.2009.03.070.

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21

Rademann, Jörg, Ahsanullah Ahsanullah, Abbas Hassan, and Farzana L. Ansari. "Integration of C-Acylation in the Solid-Phase Synthesis of Peptides and Peptidomimetics Employing Meldrum’s Acid, Phosphorus, and Sulfur Ylides." Synthesis 54, no. 06 (2021): 1503–17. http://dx.doi.org/10.1055/a-1667-3648.

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AbstractThe modification of native peptides to peptidomimetics is an important goal in medicinal chemistry and requires, in many cases, the integration of C-acylation steps involving amino acids with classical peptide synthesis. Many classical C-acylation protocols involving Claisen condensations and the use of ylides are not compatible with peptide synthesis, mostly due to the requirements for strong bases leading to epimerization or deprotection of peptides. Meldrum’s acid as well as several specific phosphorus and sulfur ylides, however, are acidic enough to provide reactive C-nucleophiles

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22

Zhang, Kai, Liang-Qiu Lu, and Wen-Jing Xiao. "Recent advances in the catalytic asymmetric alkylation of stabilized phosphorous ylides." Chemical Communications 55, no. 60 (2019): 8716–21. http://dx.doi.org/10.1039/c9cc02831e.

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23

Suchandra, Chakraborty, Basu Kaushik, and Saha Chandan. "Distinction between the reactivity of phosphorus ylide vs sulfur ylide with the carbonyl compounds : Simplicity and logic." Education in Chemical Science and Technology Vol. 2, Aug 2022 (2022): 9–24. https://doi.org/10.5281/zenodo.6813268.

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Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, Kolkata-700 073, India E-mail : cskatichandan@gmail.com Department of Chemistry, St. Paul's Cathedral Mission College, Kolkata-700 009, India Wittig olefination and Corey-Chaykovsky epoxidation of carbonyl compounds are well-documented classical and synthetically useful name reactions which are taught in great details in both undergraduate and post-graduate curricula of organic chemistry. Whilst similar reagents (a phosphorus ylide in Wittig olefination and a sulfur ylide in Corey-Chaykovsky epoxidation) and

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24

Jochem, Georg, та Alfred Schmidpeter. "Phosphonio-substituierte 1,3-Diphosphanaph thaline aus der a,o-Kondensation von Phosphonium-benzyliden / Phosphonio-Substituted 1,3-Diphosphanaphthalenes from the α.o-Condensation of Phosphonium-benzylides". Zeitschrift für Naturforschung B 51, № 6 (1996): 773–77. http://dx.doi.org/10.1515/znb-1996-0603.

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Abstract Triphenylphosphonium 1-trimethylsilylbenzylides 1 react with the bis(dichlorophosphino)- substituted ylide 2 both at their 1- and ortho-position to yield 1,3-diphosphatetraline derivatives 4 containing two ylide and PCI units each as alternating ring members. The two PCI groups differ decisively in their spontaneous dissociation in a polar medium, as well as in their oxidation by elemental sulfur. With gallium trichloride dicationic 1,3-diphosphanaphthalenes (1,3-benzodiphosphinines) are formed, in which both phosphorus ring members achieve twocoordination and which represent a novel

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25

Haghdadi, Mina, Sakineh Asghari, and Samaneh Ramezani. "Computational study on the mechanism of the three-component reaction of dimethylacetylene dicarboxylate and triphenylphosphine with 2-acetylbutyrolactone." Canadian Journal of Chemistry 93, no. 6 (2015): 666–72. http://dx.doi.org/10.1139/cjc-2014-0475.

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The molecular mechanism of the three-component reaction of triphenylphosphine, dialkyl acetylene dicarboxylate, and 2-acetylbutyrolactone to synthesize the stabilized phosphorus ylide and 1,3-butadiene derivative via the intramolecular Wittig reaction has been investigated using the density functional theory method at the B3LYP/6-31G level of theory. Two possible reaction pathways have been characterized in detail to form the cyclobutene intermediate and in the next step; the cyclobutene intermediate undergoes the conrotatory ring-opening reaction to produce the 1,3-butadiene derivative along

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26

Koike, Taichi, Jhen-Kuei Yu, and Max M. Hansmann. "Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer." Science 385, no. 6706 (2024): 305–11. http://dx.doi.org/10.1126/science.ado4564.

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Precise modification of a chemical site in a molecule at the single-atom level is one of the most elegant yet difficult transformations in chemistry. A reagent specifically designed for chemoselective introduction of monoatomic carbon is a particularly formidable challenge. Here, we report a straightforward, azide-free synthesis of a crystalline and isolable diazophosphorus ylide, Ph 3 PCN 2 , a stable compound with a carbon atom bonded to two chemically labile groups, triphenylphosphine (PPh 3 ) and dinitrogen (N 2 ). Without any additives, the diazophosphorus ylide serves as a highly selecti

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27

Krämer, Felix, Michael Radius, Helga Berberich, Israel Fernández, and Frank Breher. "A neutral, acyclic, borataalkene-like ligand for group 11 metals: L- and Z-type ligands side by side." Chemical Communications 58, no. 24 (2022): 3905–8. http://dx.doi.org/10.1039/d2cc00199c.

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Side by side! An α-borylated phosphorus ylide can act as L- and Z-type ligand side by side. A detailed experimental and computational study provides evidence for a tuneable L/Z-ratio by varying the metal fragments and/or the boron substituents.

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28

Soliman, Fouad M., and Medhat M. Said. "Chemistry of Phosphorus Ylides, 11." Zeitschrift für Naturforschung B 46, no. 8 (1991): 1105–9. http://dx.doi.org/10.1515/znb-1991-0821.

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The reaction of 1-hydroxyxanthenone (1) and hydroxyquinoline (10, 13) Mannich bases with the reactive phosphacumulated ylides (2), represents a new way for the synthesis of the pyranones and pyranthiones (5, 11, 14). On the other hand, the stabilized phosphorus ylides (6) affect the transylidation of the Mannich base (1) to the corresponding phosphoranylidenes (9). The structure of the resulting new compounds has been confirmed through elemental analysis and spectroscopic results (IR, 1H, 31P NMR and MS).

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29

Soliman, Fouad, Ibrahim Abd-Ellah, Soher Maigali, and Gamal Abd-El-Naim. "Chemistry of Phosphorus Ylides. Part 27. Metal Complexes of 4-hydroxyquinaldine, its Mannich Base and Phosphonium Ylide." Journal of Chemical Research 2009, no. 5 (2009): 277–82. http://dx.doi.org/10.3184/030823409x440841.

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The reaction of Hg2+,Cd2+,Co2+, and Ni2+ ions with 1 mol of the ligands 2-methylquinoline-4-ol,3[(diethylamino)methyl]-2-methylquinoline-4-ol, and methyl-3-(4-hyrdoxy-2-methylquinoline-3-yl)-2-(triphenylphosphoranylidene)propanoate, has been investigated to give the corresponding 1:1 metal:ligand complexes. Reaction of 2 mol of the ligand gave the corresponding 1:2 metal:ligand complexes. The coordination takes place only through the quinoline nitrogen atom. The spectroscopic and the physicochemical data of the new metal complexes are discussed.

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30

Grützmacher, Hansjörg. "Spaltung der Ylid-Bindung in Phosphor-Yliden: Photolyse von thiophosphoranylsubstituierten (Triphenylphosphoranyliden)methanen / Cleavage of Ylidic Bonds in Phosphorus Ylides: Photolysis of Thiophosphoranyl-Substituted (Triphenylphosphoranylidene)methanes." Zeitschrift für Naturforschung B 45, no. 2 (1990): 170–74. http://dx.doi.org/10.1515/znb-1990-0210.

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The thiophosphoranyl-substituted (triphenylphosphoranylidene)methanes 1, 6a, b are cleaved photolytically (λ &gt; 300 nm, 3 d, 0 °C) to yield triphenylphosphane and the thio-aza-phosphetanes 3 and 8 a, b, b′, respectively. The formation of these heterocycles is explained invoking insertion of the carbenes 2 and 7 a, b into the methine CH bond of one of the isopropyl groups. If 6a is irradiated for 16 h in the presence of the phosphanes P(NMe2)3, P(OMe)3 or P(nBu)3, the new ylides 9 a, b, c are obtained along with small quantities of 8 a. These results indicate a cleavage of the ylidic bond

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31

Nakazawa, Hiroshi, Mitsuru Kishishita, Tadahiro Nakamoto, Norihiko Nakamura, Takeshi Ishiyama, and Katsuhiko Miyoshi. "Phosphorus Ylide Migration from Fe to a Phosphenium Phosphorus." Chemistry Letters 29, no. 3 (2000): 230–31. http://dx.doi.org/10.1246/cl.2000.230.

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32

Uson, Rafael, Antonio Laguna, Mariano Laguna, Alfredo Uson, Peter G. Jones, and Cristina Freire Erdbruegger. "Bimetallic phosphorus ylide gold-silver complexes." Organometallics 6, no. 8 (1987): 1778–80. http://dx.doi.org/10.1021/om00151a026.

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33

Habibi-Khorassani, Sayyed Mostafa, Ali Ebrahimi, Malek Taher Maghsoodlou, et al. "Theoretical Study, An Efficient Synthesis Route to, and Kinetic Investigation of, Stable Phosphorus Ylides Derived from Benzamide." Progress in Reaction Kinetics and Mechanism 34, no. 3 (2009): 261–88. http://dx.doi.org/10.3184/146867809x466771.

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The synthesis, theoretical study and a kinetics and mechanistic investigation are described as a one-pot condensation reaction between benzamide and acetylenic esters in the presence of triphenyphosphine to generate a novel stable phosphorus ylides. For the first time, theoretical calculations have been employed to assign the most stable isomers ( Z or E) of phosphorus ylides 4a-c by AIM and NBO theory, in which Z-4(a,b) are the more stable forms, whereas Z-4c appears as a single isomer. In these cases, the 1H, 13C and 31P NMR spectra of these ylides are consistent with the results obtained fr

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34

Dreihäupl, Karl-Heinz, Andreas Bauer, and Hubert Schmidbaur. "Bis(silylation) of Tris(dimethylamino)phosphonium Methylide." Zeitschrift für Naturforschung B 52, no. 6 (1997): 674–78. http://dx.doi.org/10.1515/znb-1997-0602.

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Abstract Treatment of (Me2N)3PCHSiMe3 with Me3SiOTf (OTf = triflate) affords the phosphonium salt [(Me2N)3PCH(SiMe3)2]OTf (2a), which can be converted into the corresponding ylide (Me2N)3PC(SiMe3)2 (3a) in high yield using NaN(SiMe3)2. The compounds with SiMe2Ph substituents (2, 3b) are obtained following an analogous procedure. The ylide (Me2N)3PC[Si(OMe)3]2 (3c) is available in 50% yield by direct transylidation of (MeO)3SiOTf with (Me2N)3PCH2 in the molar ratio 2:3, with [(Me2N)3PMe]OTf as the by-product. Compound 3c is a distillable liquid, but 3a,b are crystalline solids the structure o

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Steiner, Matthias, Hansjörg Grützmacher, Matthias Steiner, Hansjörg Grützmacher, Hans Prtizkow та Laszlo Zsolnai. "α-Zincated phosphorus ylides". Chemical Communications, № 2 (1998): 285–86. http://dx.doi.org/10.1039/a704248e.

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Ghonchepour, Ehsan, Constantinos G. Neochoritis, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Mohammad R. Islami, and Alexander Dömling. "Glycoconjugates via Phosphorus Ylides." European Journal of Organic Chemistry 2019, no. 22 (2019): 3632–35. http://dx.doi.org/10.1002/ejoc.201900434.

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Tsuchiya, Shinji, Shun-ichi Mitomo, Hideo Kise, and Manabu Senō. "Formation reactions of phosphorus ylide–tetracyanoquinodimethane complexes." J. Chem. Soc., Perkin Trans. 2, no. 2 (1986): 245–47. http://dx.doi.org/10.1039/p29860000245.

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Berno, Pietro, Sandro Gambarotta, Sirpa Kotila, and Gerhard Erker. "Novel vanadium and titanium phosphorus ylide complexes." Chemical Communications, no. 6 (1996): 779. http://dx.doi.org/10.1039/cc9960000779.

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Li, Xiaoyan, Aichen Wang, Hongjian Sun, et al. "Effect of Different Bases and Phosphorus Ylide on the Selective Deprotonation of Phosphorus Ylide Adduct Cp*TaCl4(CH2PPh3)." Organometallics 26, no. 14 (2007): 3456–60. http://dx.doi.org/10.1021/om0701266.

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Babu, Kaki Raveendra, Yang Li, Wenbo Xu, Yuhai Tang, Wenquan Zhang, and Silong Xu. "Multicomponent benzannulation of allylic P-ylides with isocyanates or aldehydes for construction of anilines and biaryls." Chemical Communications 56, no. 62 (2020): 8865–68. http://dx.doi.org/10.1039/d0cc03461d.

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Avery, Thomas D., Ben W. Greatrex, Dennis K. Taylor, and Edward R. T. Tiekink. "Exploitation of ylide steric bulk to alter cyclopropanation outcome during the reaction of 1,2-dioxines and stabilised phosphorus ylides." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (2000): 1319–21. http://dx.doi.org/10.1039/b001975p.

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Sabounchei, Seyyed Javad, Marjan Hosseinzadeh, Ali Hashemi, Sadegh Salehzadeh, and Farahnaz Maleki. "P,C-Chelation versus P,P-coordination of unsymmetrical phosphorus ylides in palladacyclopropa[60]fullerene complexes; synthetic, spectroscopic, and theoretical studies." Dalton Transactions 45, no. 35 (2016): 13899–906. http://dx.doi.org/10.1039/c6dt02332k.

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Zhang, Xinzhi, Yangyang Zhang, Cuijian Liang, and Jun Jiang. "Copper-catalyzed P–H insertion reactions of sulfoxonium ylides." Organic & Biomolecular Chemistry 19, no. 26 (2021): 5767–71. http://dx.doi.org/10.1039/d1ob00948f.

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Babu, Kaki Raveendra, Wendan Han, Jian-Bo Chen, et al. "A three-component reaction of phosphorus ylides with isocyanates: facile synthesis of 2-amino-3-carboxylate-4-quinolones." Chemical Communications 56, no. 44 (2020): 5909–12. http://dx.doi.org/10.1039/d0cc01401j.

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Kim, Ko Hoon, Sangku Lee, Junseong Lee та Jae Nyoung Kim. "Synthesis of Ramirez ylides from Morita–Baylis–Hillman adducts of α-bromocinnamaldehyde: an intramolecular 1,6-conjugate addition of phosphorus ylide". Tetrahedron Letters 56, № 29 (2015): 4349–53. http://dx.doi.org/10.1016/j.tetlet.2015.05.083.

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Liu, Shen, Wenteng Chen, Jing Luo, and Yongping Yu. "[3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines." Chem. Commun. 50, no. 62 (2014): 8539–42. http://dx.doi.org/10.1039/c4cc03462g.

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Tandem Michael addition and Witting or Horner–Wadsworth–Emmons olefination initiated [3+3] annulation between vinyl azides and allylic phosphorus ylides or allylic phosphoryl-stabilized carbanions has been developed.

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Mosslemin, Mohammad H., Masoumeh Tabatabaee, Alireza Hassanabadi, and Asal Lamei. "Three-Component Reaction of Triphenylphosphine, Acetylenic Esters and 4-(Arylideneamino)-3-ethyl-1H-1,2,4-triazole-5(4H)-thiones for the Synthesis of Phosphorus Ylides." E-Journal of Chemistry 8, s1 (2011): S27—S32. http://dx.doi.org/10.1155/2011/860189.

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Triphenylphosphine reacts with ‎4-(arylideneamino)-3-ethyl-1H-1,2,4-triazole-5(4H)-thiones in the presence of dialkyl acetylenedicarboxylates to produce highly functionalized, salt-free phosphorus ylides in excellent yields.

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Yavari, Issa, Malek Taher Maghsoodlou, Hoorih Djahaniani, and Norollah Hazeri. "A Facile Synthesis of Stable Heterocyclic Phosphorus Ylides." Journal of Chemical Research 23, no. 3 (1999): 216–17. http://dx.doi.org/10.1177/174751989902300323.

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Stable crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylate and strong NH-acids, such as imidazole, benzimidazole, benzotriazole or carbazole.

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Romanenko, E. A. "Structural features of the phosphorus heterocumulene ylides (sp-ylides)." Russian Journal of General Chemistry 77, no. 3 (2007): 421–28. http://dx.doi.org/10.1134/s1070363207030152.

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Kolodyazhnyi, O. I. "P-Halogen-substituted phosphorus ylids." Russian Chemical Reviews 60, no. 4 (1991): 391–409. http://dx.doi.org/10.1070/rc1991v060n04abeh001084.

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