European Journal of Inorganic Chemistry

Cover image for Vol. 2016 Issue 5

Special Issue: Special Issue: Low-Coordinate Phosphorus Compounds (Cluster Issue)

February 2016

Volume 2016, Issue 5

Pages 562–773

Issue edited by: Christian Müller

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Cover Picture: Low-Coordinate Phosphorus Compounds (Eur. J. Inorg. Chem. 5/2016)

      Christian Müller

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201690008

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      The cover picture, designed by Guest Editor Christian Müller, shows the original paper published in Angew. Chemie in 1966 of the synthesis of the first low-coordinate organophosphorus compound, 2,4,6-triphenylphosphabenzene, by Gottfried Märkl. The structure of the stable yellow crystalline compound is also depicted. This communication was central in changing the way the bonding around phosphorus atoms was viewed, and the demonstration that hybridization was possible for phosphorus led to many reports on formally sp2-hybridized phosphorus(III) compounds with significantly different properties from those of classical trivalent phosphorus species.

  2. Cover Profile

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Synthesis and Photoluminescence Properties of CuI Complexes with Chelating Phosphinito Phosphinine Ligands (page 562)

      Xiaodan Chen, Zhongshu Li, Fan Yanan and Hansjörg Grützmacher

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201600071

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      The most remarkable aspect is that the low-coordinate phosphorus center of the phosphinine ring resides in the bridging position between the two Cu centers...

      Read more about the story behind the cover in the Cover Profile and about the research itself on p. 633 ff.

  3. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Inside Cover: Low-Coordinate Phosphorus Compounds (Eur. J. Inorg. Chem. 5/2016)

      Anup K. Adhikari, Toni Grell, Peter Lönnecke and Evamarie Hey-Hawkins

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201690010

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      The inside cover picture shows the attempt to stabilize the highly reactive tetramesityltetraphosphanediide anion (P4Mes42–, Mes = 2,4,6-Me3C6H2) by adduct formation with an N-heterocyclic carbene (NHC). However, rather than forming the expected stable adduct, the attack of the NHCs rips the tetraphosphanediide chain apart to produce two neutral carbene–phosphinidenes and a P2Mes22– dianion, which is not “trapped” with NHC. Details are discussed in the Communication by E. Hey-Hawkins et al. on p. 620 ff.

    2. Back Cover: Low-Coordinate Phosphorus Compounds (Eur. J. Inorg. Chem. 5/2016)

      Xiaodan Chen, Zhongshu Li, Fan Yanan and Hansjörg Grützmacher

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201690011

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      The back cover picture shows the synthesis of dinuclear copper(I) halide complexes from a new diphenylphosphinite phosphinine as chelating ligand and simple CuI halides. Remarkably, it is the phosphorus center, and not the halide, that bridges the Cu centers. These complexes show phosphorescence in the range 658–702 nm in the solid state at room temperature. The emission can be tuned by changing the terminal halide ligand. Details are discussed in the Communication by Z. Li, H.-J. Grützmacher et al. on p. 633 ff. For more on the story behind the cover research, see the Cover Profile.

  4. News

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
  5. Editorial

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Editorial

      Low-Coordinate Phosphorus Chemistry Has Come a Long Way (pages 567–568)

      Karen Hindson

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201600067

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      Editor Karen Hindson introduces this Cluster Issue on low-coordinate phosphorus compounds including papers highlighting the present state of the field after fifty years of development since the synthesis of the first low-coordinate phosphorus compound in 1966.

  6. Guest Editorial

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. The Papers in This Issue

      Low-Coordinate Phosphorus Compounds (pages 569–571)

      Christian Müller

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201600057

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      Guest Editor Christian M�ller presents an overview of the papers in this Cluster Issue on the occasion of the fiftieth anniversary of the synthesis of the first low-coordinate organophosphorus compound by Gottfried M�rkl in 1966.

  7. Essay

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Low-Coordinate Phosphorus Compounds

      The Route to Phosphabenzene and Beyond (pages 572–574)

      Arthur J. Ashe III

      Article first published online: 12 FEB 2016 | DOI: 10.1002/ejic.201600007

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      This essay recalls the author's syntheses of phosphabenzene, arsabenzene, stibabenzene, and bismabenzene in 1971 and 1972.

  8. Microreviews

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Heterophospholes

      Electron-Rich Aromatic 1,3-Heterophospholes – Recent Syntheses and Impact of High Electron Density at σ2P on the Reactivity (pages 575–594)

      Joachim W. Heinicke

      Article first published online: 10 NOV 2015 | DOI: 10.1002/ejic.201500941

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      The synthesis, properties, and reactivity of π-excess aromatic σ2P-heterocycles containing the X–C=P–C motif are reviewed. High electron density at σ2P gives these compounds a special position among the σ2P-heterocycles, allowing CH- and NH-lithiation, ambident reactivity of the anions, P-alkylation, catalytic P-arylation, and exclusively μ2- and/or tilted η1-P-coordination in d10 metal complexes.

    2. Triazaphospholes

      Recent Developments in the Chemistry of 3H-1,2,3,4-Triazaphos­phole Derivatives (pages 595–606)

      Julian A. W. Sklorz and Christian Müller

      Article first published online: 7 DEC 2015 | DOI: 10.1002/ejic.201500976

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      This microreview provides an overview of recent developments in the chemistry of pyridyl-functionalized 3H-1,2,3,4-triazaphospholes. Access to new chelating, low-coordinate phosphorus heterocycles could lead to a much broader scope for potential applications. New developments in areas such as homogeneous catalysis and phosphorus-containing molecular materials can be foreseen in the near future.

    3. Diphosphenes

      Sterically Protected Diphosphenes (pages 607–615)

      Masaaki Yoshifuji

      Article first published online: 2 DEC 2015 | DOI: 10.1002/ejic.201500990

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      (E)-Bis(2,4,6-tri-tert-butylphenyl)diphosphene was prepared in 1981 for the first time, as a stable compound containing an isolated low-coordinate P=P bond. Since then many sterically protected diphosphenes with various substituents have been prepared, showing remarkable physicochemical features and interesting chemical reactivity.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Terminal Phosphinidenes

      The Reaction of Terminal Phosphinidene Complexes [RP–W(CO)5] with Vinylbor­onic Acids: Cycloaddition vs. P–C Bond Formation (pages 616–619)

      Yong Xiang Ng and François Mathey

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejic.201500594

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      Terminal phosphinidene complexes react with vinylboronic acid to give the expected phosphirane complexes, but the addition of K3PO4 changes the course of the reaction, and secondary vinylphosphine complexes are obtained instead.

    2. Tetraphosphanediides

      Formation of a Carbene–Phosphinidene Adduct by NHC-Induced P–P Bond Cleavage in Sodium Tetramesityltetraphosphanediide (pages 620–622)

      Anup K. Adhikari, Toni Grell, Peter Lönnecke and Evamarie Hey-Hawkins

      Article first published online: 8 OCT 2015 | DOI: 10.1002/ejic.201500952

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      The reaction of [Na2(thf)4P4Mes4] (Mes = 2,4,6-Me3C6H2) with 1,3-dimethylimidazolin-2-ylidene (Me2Im) or the corresponding imidazolium iodide ([Me2ImH]I) leads to P–P bond cleavage and formation of the carbene–phosphinidene adduct (Me2Im)PMes.

    3. Phosphinoalumanes

      Synthesis and Structure of Lewis-Base-Free Phosphinoalumane Derivatives (pages 623–627)

      Tomohiro Agou, Shin Ikeda, Takahiro Sasamori and Norihiro Tokitoh

      Article first published online: 13 NOV 2015 | DOI: 10.1002/ejic.201501141

      Thumbnail image of graphical abstract

      Lewis-base-free diphosphinoalumane and 1-hydro-2-chlorophosphinioalumane derivatives bearing a bulky aryl substituent were synthesized from the corresponding lithium phosphide and dichloroalumane. Their structures were determined spectroscopically and by X-ray crystallography. Because of the efficient steric protection by the bulky aryl substituent, their aluminum centers are tricoordinate.

    4. Synthesis of Phosphinines

      Reduction of λ5-Phosphinines (pages 628–632)

      Aleksandr Savateev, Yurii Vlasenko, Nataliya Shtil and Aleksandr Kostyuk

      Article first published online: 13 OCT 2015 | DOI: 10.1002/ejic.201500856

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      A set of parent λ5-phosphinines bearing OMe, SMe, and/or NMe2 substituents was synthesized. It was shown that they could be readily reduced to parent λ3-phosphinine. The most convenient method appeared to be reduction of readily available λ5-phosphinine featuring the dimethylamino groups. Its congener featuring the diethylamino group does not react under analogous conditions at all.

    5. Photoluminescence

      Synthesis and Photoluminescence Properties of CuI Complexes with Chelating Phosphinito Phosphinine Ligands (pages 633–638)

      Xiaodan Chen, Zhongshu Li, Fan Yanan and Hansjörg Grützmacher

      Article first published online: 9 NOV 2015 | DOI: 10.1002/ejic.201500933

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      Dinuclear copper(I) halide complexes with a new diphenylphosphinite phosphinine as chelating ligand were prepared. They show tunable phosphorescence in the range 650–700 nm in the solid state at room temperature.

  10. Full Papers

    1. Top of page
    2. Cover Picture
    3. Cover Profile
    4. Cover Picture
    5. News
    6. Editorial
    7. Guest Editorial
    8. Essay
    9. Microreviews
    10. Communications
    11. Full Papers
    1. Phosphathioethynolates

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      Ambient-Temperature Synthesis of 2-Phosphathioethynolate, PCS, and the Ligand Properties of ECX (E = N, P; X = O, S) (pages 639–648)

      Andrew R. Jupp, Michael B. Geeson, John E. McGrady and Jose M. Goicoechea

      Article first published online: 4 NOV 2015 | DOI: 10.1002/ejic.201501075

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      We report a synthesis of the 2-phosphathioethynolate anion, PCS, under ambient conditions. The coordination chemistry of PCO, PCS and their nitrogen-containing congeners is also explored.

    2. Phosphaalkenes

      Direct Access to Inversely Polarized Phosphaalkenes from Elemental Phosphorus or Polyphosphides (pages 649–658)

      Mario Cicač-Hudi, Johannes Bender, Simon Hugo Schlindwein, Mark Bispinghoff, Martin Nieger, Hansjörg Grützmacher and Dietrich Gudat

      Article first published online: 22 OCT 2015 | DOI: 10.1002/ejic.201501017

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      The one-step syntheses of imidazoyl phosphinidenes and bis(imidazolyl)–P(I) halides from elemental phosphorus or Na3P7 and (Me3Si)3P7 are described. The heptaphosphides are obtained from P4 and Pred in excellent yields by a safe and simple method. The breakdown of P4 involves the participation of N-heterocyclic carbenes (NHCs) and tBuOH.

    3. Phosphorane Synthesis

      Hydride Abstraction and Deprotonation – an Efficient Route to Low Coordinate Phosphorus and Arsenic Species (pages 659–666)

      Laurence J. Taylor, Michael Bühl, Piotr Wawrzyniak, Brian A. Chalmers, J. Derek Woollins, Alexandra M. Z. Slawin, Amy L. Fuller and Petr Kilian

      Article first published online: 6 OCT 2015 | DOI: 10.1002/ejic.201500948

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      Hydride abstraction from a primary phosphine/arsine affords the first examples of secondary phosphino/arsino-phosphonium salts. Subsequent deprotonation provides a novel and high yielding route to phosphine-stabilised phosphinidene/arsinidene. These investigations indirectly support an ionic mechanism for the spontaneous dehydrogenation of the primary arsine.

    4. White Phosphorus Activation

      Reaction of P4 with in situ Formed cyclo-Triphosphatriazenium Cation [(DmpNP)3Cl2]+ (Dmp = 2,6-Dimethylphenyl) (pages 667–677)

      Michael H. Holthausen, Chris Sala and Jan J. Weigand

      Article first published online: 28 OCT 2015 | DOI: 10.1002/ejic.201500875

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      The controlled reaction of P4 with in situ formed cyclo-triphosphatriazenium cation [(DmpNP)3Cl2]+ (Dmp = 2,6-dimethylphenyl) leads to the formation of mono- and dicationic derivatives [(DmpNP)3(P4)Cl2]+ and [(DmpNP)3(P4)2Cl]2+. The insertion reaction proceeds via a dicoordinate, cyclic phosphenium cation.

    5. Se-Substituted Phosphaalkenes

      Selenium-Substituted Phosphaalk­enes Obtained through 1,2-Elimination of Chlorosilanes from Selenen­ylchlorophosphines (pages 678–684)

      Takahiro Sasamori, José Manuel Villalba Franco, Jing-Dong Guo, Koh Sugamata, Shigeru Nagase, Rainer Streubel and Norihiro Tokitoh

      Article first published online: 21 DEC 2015 | DOI: 10.1002/ejic.201500989

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      Stable selenenyl-chlorophosphines, bearing a trisilylalkyl group, were synthesized, and their treatment with Lewis acids such as AlCl3 afforded the corresponding phosphaalkenes. The experimental results and theoretical calculations suggested that the reaction proceeds through the intramolecular 1,2-elimination of chlorosilanes

    6. Phosphinidene Adducts

      Reactions of Li/Cl Phosphinidenoid Complexes with 1,3,4,5-Tetramethylimidazol-2-ylidene: A New Route to N-Heterocyclic Carbene Adducts of Terminal Phosphin­idene Complexes and an Unprecedented Transformation of an Oxaphosphirane Complex (pages 685–690)

      Melina Klein, Gregor Schnakenburg, Arturo Espinosa Ferao, Norihiro Tokitoh and Rainer Streubel

      Article first published online: 25 NOV 2015 | DOI: 10.1002/ejic.201500959

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      Reaction of P-Cl phosphinidenoid complexes and an oxaphosphirane complex with an N-heterocyclic carbene (NHC) to give a new zwitterionic phosphaalkene complex is described; the last-named can also be regarded as an NHC adduct of a terminal phosphinidene complex.

    7. P–C Cages

      Optically Active P5-Deltacyclenes: A Unique Cage-Inversion Reaction and Some Transition-Metal Complexes of the Rearranged Cage (pages 691–699)

      Christine Höhn, Walter Bauer, Frank W. Heinemann, Sergi Huguet Torrell, Irene C. Keller, Lars Rohwer, Tatyana E. Shubina and Ulrich Zenneck

      Article first published online: 13 NOV 2015 | DOI: 10.1002/ejic.201501015

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      Cage-chiral P–C cage compounds are a new class of chiral ligands. A stereoselective rearrangement performed with highly enriched P5-deltacyclene enantiomers is accompanied by a unique cage inversion, which results in almost mirror-symmetric CD curves of related pairs of P5-deltacyclene/iso-P5-deltacyclene enantiomers. The absolute structure of a W(CO)5 complex enantiomer confirms the observation.

    8. Tetraphosphane Ligands

      Serendipitous CO- and RhI-Induced ­Coupling of Bidentate Phosphaalkenes with Expulsion of Bis(trimethylsilyl)ketene Leading to RhIII-Coordinated Dianionic Tetradentate Ligands (pages 700–708)

      Daniela Lungu, Roxana M. Bîrzoi, Christine Goers, Rainer Bartsch, Wolf-W. du Mont, Constantin Daniliuc and Peter G. Jones

      Article first published online: 8 OCT 2015 | DOI: 10.1002/ejic.201500817

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      The reaction of [RhCl(CO)(PPh3)2] with bidentate phosphaalkene ligands 1 [(Me3Si)2C=PN(R)PPh2; 1a: R = 1-Ada; 1b: R = tBu] leads, with elimination of bis(trimethylsilyl)ketene, to racemic RhIII–chloro complexes [RhCl({Ph2PN(R)P}2C(SiMe3)2)] (11a,b) each containing a dianionic η4-coordinated ligand. CO is essential for the unusual ligand coupling reaction.

    9. Unsaturated P Compounds

      The Heavier Analogues of Alkenes: A Theoretical Comparison of Unsaturated Group 15/14 Systems (pages 709–717)

      Djawed Nauroozi and Andreas Orthaber

      Article first published online: 21 OCT 2015 | DOI: 10.1002/ejic.201500848

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      The theoretical study of phosphaalkenes, iminophosphanes, and diphosphenes in comparison with their alkene and imine analogues, reveals the impact of different substitutions on the electronic, spectroscopic, and structural properties of the phosphorus-containing heteroalkenes.

    10. Silylated Phospholes

      A Rational Synthetic Approach to 2,5-Diphenyl-β-silyl Phospholes (pages 718–725)

      Dieter Klintuch, Kristijan Krekić, Clemens Bruhn, Zoltán Benkő and Rudolf Pietschnig

      Article first published online: 4 NOV 2015 | DOI: 10.1002/ejic.201500874

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      Tuning the fluorescence of phospholes is possible by placing silyl units in the β-position. A general access to these compounds has been opened by modification of a classical procedure.

    11. Heterophospholes

      Synthesis of 2-Phosphaindolizine and [1,3]Azaphospholo[1,5-a]quin­oline (pages 726–735)

      Christina Hettstedt, Robert J. Mayer, Jörn F. Martens, Sarah Linert and Konstantin Karaghiosoff

      Article first published online: 15 DEC 2015 | DOI: 10.1002/ejic.201501120

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      A synthetic procedure for preparing 1- and 3-unsubstituted 2-phosphaindolizines has been developed. This new method starts from ClCH2Cl2, PicolylTMS or QuinaldinylTMS and a base to form the desired azaphosphole as the only phosphorus-containing species.

    12. Phosphacyclobutadiene Complexes

      Cobalt(I) and Nickel(II) Complexes of Bis(1,3-diphosphacyclobutadiene) Sandwich Anions (pages 736–742)

      Christian Rödl and Robert Wolf

      Article first published online: 14 JUL 2015 | DOI: 10.1002/ejic.201500583

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      Dinuclear diphosphacyclobutadiene complexes have been synthesized by transmetalating the thallium(I) salt [Tl(thf)2{Co(P2C2tBu2)2}] with organometallic cobalt(I) and nickel(II) halides. The structural, spectroscopic, and redox properties of two new bimetallic complexes are presented, and their electronic structures are analyzed by DFT calculations.

    13. Phosphaferrocene Derivatives

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      The First Coordination Polymers Based on 1,3-Diphosphaferrocenes and 1,1′,2,3′,4-Pentaphosphaferrocenes (pages 743–753)

      Claudia Heindl, Sabine Reisinger, Christoph Schwarzmaier, Lena Rummel, Alexander V. Virovets, Eugenia V. Peresypkina and Manfred Scheer

      Article first published online: 8 OCT 2015 | DOI: 10.1002/ejic.201500873

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      A synthetic approach to a series of iPr-substituted phosphaferrocenes was found. Their self-assembly with CuI halides led to one- and two-dimensional polymers: 1D chains containing the 1,3-diphosphaferrocene, 1D ladderlike structures with the 1,1′,2,3′,4-pentaphosphaferrocene, and 2D meshlike networks bearing the 1,2,4-triphosphaferrocene.

    14. Phosphaalkene Complexes

      Iridium(I) Complexes Bearing a Noninnocent PNP-Pincer-Type Phosphaalkene ­Ligand: Catalytic Application in the Base-Free N-Alkylation of Amines with Alcohols (pages 754–760)

      Yung-Hung Chang, Ippei Tanigawa, Hiro-omi Taguchi, Katsuhiko Takeuchi and Fumiyuki Ozawa

      Article first published online: 29 SEP 2015 | DOI: 10.1002/ejic.201500900

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      PNP-pincer-type phosphaalkene complexes of IrI bearing a dearomatized pyridine ring have been found to catalyze the dehydration/condensation of amines with alcohols under base-free conditions to afford N-alkylated amines and imines in high yields. The product selectivity can be controlled by the choice of auxiliary ligands (L) as well as the reaction conditions.

    15. Luminescent Complexes

      Synthesis and Luminescence Properties of Cycloplatinated Complexes with a Chelating NC Pyridine-Derived N-Heterocyclic Carbene – Influence of 2,4,6-Triphenyl­phosphinine versus Triphenylphosphine (pages 761–767)

      Jamal Moussa, Gemma R. Freeman, J. A. Gareth Williams, Lise-Marie Chamoreau, Patrick Herson and Hani Amouri

      Article first published online: 30 OCT 2015 | DOI: 10.1002/ejic.201500879

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      Two cycloplatinated complexes with a rare bidentate pyridylpyridylidene NC ligand and triphenylphosphine or 2,4,6-triphenylphosphinine coligands are synthesised and characterised. The phosphinine compound is strongly phosphorescent at 77 K, in contrast to the triphenylphosphine counterpart; this behaviour is probably the result of the exceptional π-acceptor ability of the phosphabenzene ring.

    16. Azaphospholes

      Synthesis of a Luminescent Azaphosphole (pages 768–773)

      Shanshan Wu, Arnold L. Rheingold, James A. Golen, Alexandra B. Grimm and John D. Protasiewicz

      Article first published online: 21 JAN 2016 | DOI: 10.1002/ejic.201501279

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      A carbazole-based azaphosphole (compound 3) has been prepared by acid-catalyzed dehydrocyclization of 1-phosphino-9H-carbazole (2) with benzoyl chloride. Compounds 2 and 3 display significant fluorescence in solution.

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