Carbaborane-substituted 1,2,3-triphospholanes and 1-aza-2,5-diphospholane: new synthetic approaches.

New phosphorus-containing, five-membered P,P,P and P,N,P heterocycles were synthesized and fully characterized. The P,P,P heterocycles, 1,2,3-triphospholanes, can be synthesized by two different facile pathways, whereas the P,N,P compound, a 1-aza-2,5-diphospholane, can only be obtained with silylamine.

[1]  E. Hey‐Hawkins,et al.  Endocyclic P-P bond cleavage in carbaborane-substituted 1,2-diphosphetane: a new route to secondary phosphinocarbaboranes. , 2012, Chemical communications.

[2]  Lawrence J Marnett,et al.  Ortho-carbaborane derivatives of indomethacin as cyclooxygenase (COX)-2 selective inhibitors. , 2012, Bioorganic & medicinal chemistry.

[3]  F. Teixidor,et al.  Relaxed but highly compact diansa metallacyclophanes. , 2011, Journal of the American Chemical Society.

[4]  Menyhárt B. Sárosi,et al.  Carbaboran-substituierte 1,2-Diphosphetane , 2011 .

[5]  E. Hey‐Hawkins,et al.  Carbaborane-substituted 1,2-diphosphetanes. , 2011, Angewandte Chemie.

[6]  E. Hey‐Hawkins,et al.  Asborin Inhibits Aldo/Keto Reductase 1A1 , 2011, ChemMedChem.

[7]  S. Stadlbauer,et al.  Chiral functionalized bisphosphine ligands: Transition metal complexes of 1,2-bis( tert -Butylchlorophosphino)-1,2-dicarba- closo -dodecaborane(12) , 2009 .

[8]  E. Hey‐Hawkins,et al.  Platinum(II) and palladium(II) complexes of chiral P-Cl functionalized bis-phosphino ortho-carbaboranes. , 2009, Inorganic chemistry.

[9]  B. Kirchner,et al.  Enantiomerically Pure Bis(phosphanyl)carbaborane(12) Compounds , 2009 .

[10]  B. Kirchner,et al.  Synthesis and reactivity of ortho-carbaborane-containing chiral aminohalophosphines. , 2009, Inorganic chemistry.

[11]  Clara Viñas,et al.  Influence of the solvent and R groups on the structure of (carboranyl)R2PI2 compounds in solution. Crystal structure of the first iodophosphonium salt incorporating the anion [7,8-nido-C2B9H10]-. , 2008, Dalton transactions.

[12]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[13]  F. Teixidor,et al.  A discrete PI--IP assembly: the large influence of weak interactions on the 31P NMR spectra of phosphane-diiodine complexes. , 2006, Angewandte Chemie.

[14]  P. Schleyer,et al.  Strikingly long C...C distances in 1,2-disubstituted ortho-carboranes and their dianions. , 2005, Journal of the American Chemical Society.

[15]  G. Bertrand,et al.  Dimerization of a Cyclo‐1σ4,3σ2,4σ2‐Triphosphapentadienyl Radical: Evidence for Phosphorus–Phosphorus Odd‐Electron Bonds , 2005 .

[16]  G. Bertrand,et al.  Dimerization of a cyclo-1sigma4,3sigma2,4sigma2-triphosphapentadienyl radical: evidence for phosphorus-phosphorus odd-electron bonds. , 2005, Angewandte Chemie.

[17]  F. Teixidor,et al.  Plasticity of the five-membered chelate ring in [PdCl2(1,2-(PR2)2-1,2-C2B10H10)] complexes (R = H or iPr) , 2005 .

[18]  A. Slawin,et al.  Naphthalene-1,8-diyl bis(halogenophosphanes): novel syntheses and structures of useful synthetic building blocks. , 2003, Chemistry.

[19]  K. Miyoshi,et al.  Naphtho[1,8-b,c]phosphete and 1,2-diphosphaacenaphthene from the reaction of 1,8-dilithionaphthalene with RPCl2. , 2002, Angewandte Chemie.

[20]  P. Granger,et al.  NMR Nomenclature: nuclear spin properties and conventions for chemical shifts (IUPAC Recommendations 2001) , 2002 .

[21]  F. Teixidor,et al.  Phosphine–boranes incorporating the carborane cluster , 2002 .

[22]  W. E. Hill,et al.  Coordination Chemistry of Silver(I) with the Nitrogen-Bridged Ligands (C6H5)2PN(H)P(C6H5)2 and (C6H5)2PN(CH3)P(C6H5)2: The Effect of Alkylating the Nitrogen Bridge on Ligand Bridging versus Chelating Behavior , 2002 .

[23]  E. Hey‐Hawkins,et al.  Synthesis and coordination properties of 1-tert-butylchlorophosphino- and 1,2-bis(tert-butylchlorophosphino)-1,2-dicarba-closo-dodecaborane(12)—molecular structures of rac- and meso-1,2-(PtBuCl)2C2B10H10 and (R,R,R,R/S,S,S,S)-[{Cu{1,2-(PtBuCl)2C2B10H10}(μ-Cl)}2] , 2001 .

[24]  C. Viňas,et al.  Contribution of the nido-[7,8-C2B9H10]- anion to the chemical stability, basicity, and 31P NMR chemical shift in nido-o-carboranylmonophosphines. , 2001, Inorganic chemistry.

[25]  H. Ang,et al.  Reactions of 1,2,3-triphenyl-1,2,3-triphosphaindan with activated triosmium carbonyl clusters: characterization and crystal structure of the products , 2001 .

[26]  A. Slawin,et al.  P–N bond formation as a route to a highly electron rich bidentate phosphine ligand and its application in homogenous catalysis , 2001 .

[27]  A. Orpen,et al.  Steric activation of chelate catalysts: efficient polyketone catalysts based on four-membered palladium(II) diphosphine chelates , 2001 .

[28]  F. Teixidor,et al.  The Distinct Effect of the o-Carboranyl Fragment: Its Influence on the I-I Distance in R3 PI2 Complexes. , 2000, Angewandte Chemie.

[29]  H. Grützmacher,et al.  BABAR‐Phos‐Rhodiumkomplexe: reversible Metallinsertion in einen dreigliedrigen Ring und katalytische Hydroborierungen , 2000 .

[30]  Grützmacher,et al.  BABAR-Phos Rhodium Complexes: Reversible Metal Insertion into a Three-Membered Ring and Catalytic Hydroborations This work was supported by the ETH Zürich and the National Swiss Science Foundation. , 2000, Angewandte Chemie.

[31]  A. Slawin,et al.  P–N bond formation as a route to highly electron rich phosphine ligands , 2000 .

[32]  A. Slawin,et al.  Molybdenum(0), ruthenium(II), palladium(II), platinum(II), copper(I) and gold (I) complexes of a new methoxy functionalised bis(phosphino)amine: synthesis and structure , 2000 .

[33]  E. Hey‐Hawkins,et al.  The reaction of phenylchlorophosphino-substituted1,2-dicarba-closo-dodecaboranes(12) with elemental sulfur and molecular structures ofrac-1,2-bis(phenylchlorophosphino)-1,2-dicarba-closo-dodecaborane(12) and 1-phenylchlorothiophosphino-2-phenyl-1,2-dicarba-closo-dodecaborane(12) , 1998 .

[34]  J. Sieler,et al.  Synthesis, molecular structure and reactivity of the first secondary carbaboranylbisphosphine 1,2-bis(phenylphosphino)-1,2-dicarba-closo-dodecaborane(12) , 1998 .

[35]  H. Nöth,et al.  Contribution to the Chemistry of Boron, 240 . Studies on Benzo‐1,3,2‐diphosphaborolanes, Benzo‐1,4,2,3‐diphosphadiborinanes and Benzo‐1,5,2,3,4‐diphosphatriborepanes , 1997 .

[36]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[37]  F. Teixidor,et al.  The formation of nido [7,8-(PR2)2-7,8-C2B9H10]− from closo 1,2−(PR2)2−1,2−C2B10H10 (): a process enhanced by complexation , 1996 .

[38]  D. Hockless,et al.  Direct Syntheses of 1-Phenylphosphetane and 1-Phenylphosphirane. Crystal and Molecular Structures of Neutral and Cationic Cyclotrimerization Precursor Complexes , 1996 .

[39]  M. A. Fox,et al.  Deboronation of C-substituted ortho- and meta-closo-carboranes using “wet” fluoride ion solutions , 1996 .

[40]  F. Teixidor,et al.  Procedure for the degradation of 1,2-(PR2)2-1,2-dicarba-closo-dodecaborane(12) and 1-(PR2)-2-R′-1,2-dicarba-closo-dodecaborane(12) , 1995 .

[41]  M. Hawthorne,et al.  Facile Electrophilic Iodination of Icosahedral Carboranes. Synthesis of Carborane Derivatives with Boron-Carbon Bonds via the Palladium-Catalyzed Reaction of Diiodocarboranes with Grignard Reagents , 1995 .

[42]  L. Ricard,et al.  Insertion of transition metals into the phosphorus-phosphorus bond of 1,2-dihydro-1,2-diphosphetes: toward the phosphorus analogs of metal dithiolene complexes , 1992 .

[43]  S. Buchwald,et al.  Transition-metal-substituted diphosphenes. 29. Cycloaddition reactions of the diphosphenyl complex (.eta.5-C5Me5)(CO)2Fe-P:P-Mes* (Mes* = 2,4,6-tert-Bu3C6H2) with hexafluoroacetone. X-ray structure analyses of (.eta.5-C5Me5)(CO)Fe-P(:PMes*)OC(CF3)2C(O) and (.eta.5-C5Me5)(CO)2Fe-P-P(Mes*)OC(CF3)2 , 1992 .

[44]  V. I. Bregadze,et al.  Dicarba-closo-dodecaboranes C2B10H12 and their derivatives , 1992 .

[45]  J. F. Nixon,et al.  Insertion reactions of [Pt(PPh3)2] fragments into the four-membered ring complex [W(CO)5PPhC(OEt)CPhCHPh]. Crystal and molecular structures of [Pt(dppe)PPh(W(CO)5)C(OEt)CPhCHPh] and [Pt(PPh3)2((W(CO)5)PhPC(OEt)CPhCHPh)(η2-PC))] , 1991 .

[46]  T. Onak,et al.  Cage opening of parent closo cage carboranes with fluoride ion: formation of 5-fluoro-hexahydro-nido-2,4-dicarbahexaborate(1-) ([5-F-nido-2,4-C2B4H6]-) , 1991 .

[47]  L. Ricard,et al.  A New Route to 1,3-Diphospholide Ions. Synthesis and X-Ray Structure Analysis of a 1,3-Diphosphaferrocene , 1990 .

[48]  F. Mathey,et al.  Ein neuer Weg zu 1,3‐Diphospholid‐Ionen; Synthese und Röntgenstrukturanalyse eines 1,3‐Diphosphaferrocens , 1990 .

[49]  R. Boese,et al.  Zur Reaktion des Diphosphenyl‐Komplexes (η5‐C5Me5)(CO)2Fe – P=P – Aryl (Aryl = 2,4,6‐tBu3C6H2) mit elektronenarmen Alkenen. Röntgenstrukturanalyse des Diphosphetans , 1990 .

[50]  F. Mathey,et al.  Reactions of 1,2-Diphosphetenes with Lithium and Lithium Alkyls. , 1986 .

[51]  Maitland Jones,et al.  9-Iodo-o-carborane , 1985 .

[52]  H. Schmidt,et al.  Reaktion des aktivierten 1,2-Diphosphinobenzens mit Diphenylcarbodiimid , 1985 .

[53]  W. S. Sheldrick,et al.  Die Reaktion von Alkaliphosphiden mit weißem Phosphor, II. Bildung und Struktur von 2‐Lithio‐2,3‐dihydro‐1,3‐diphenyl‐1H‐benzotriphosphol , 1985 .

[54]  K. Ǐssleib,et al.  Alkali‐Phosphorverbindungen und ihr reaktives Verhalten. 81. 2‐Organoelement‐1,3‐benzodiphospholene , 1984 .

[55]  F. Mathey,et al.  Exocyclic P–C vs. endocyclic P–P bond cleavage in 1,2-diphosphetes. A competition between cyclic delocalization and cyclic strain controlled by the substitution pattern , 1984 .

[56]  A. Mitschler,et al.  Preparation of 3,3',4,4'-tetramethyl-1,1'-biphospholyl and its reactions with iron and cobalt carbonyls. Synthesis and x-ray crystal structure of a phospholyl complex with a chain of four cobalt atoms , 1983 .

[57]  V. Ol’shevskaya,et al.  Synthesis of B-organo-substituted 1,2-, 1,7-, and 1,12-dicarbaclosododecarboranes(12) , 1982 .

[58]  E. Leißring,et al.  1.3-Benzodiphosphole, 1.2-bis-dimethylaminoalkylidenphosphino-benzen☆ , 1981 .

[59]  J. Satge,et al.  Dimetalla(IVB)-2,5 phospholannes et metalla(IVB)-2 diphospholannes-1,3 , 1977 .

[60]  R. King,et al.  Complexes of trivalent phosphorus derivatives. XVII. Reactions of iron carbonyls with 1,2,3-triphenyl-1,2,3-triphosphaindane , 1976 .

[61]  K. Ǐssleib,et al.  Alkali-Phosphorverbindungen und ihr reaktives Verhalten LXXII. 2-Organoelement-1,3-Diphospholane und -Phosphorinane Teil II , 1976 .

[62]  K. Ǐssleib,et al.  Alkali‐Phosphorverbindungen und ihr reaktives Verhalten. LXXII. 2‐Organoelement‐1, 3‐diphosphorinane‐ sowie ‐diphospholane , 1974 .

[63]  F. G. Mann,et al.  Further studies in the chemistry of 2,3-dihydro-1,2,3-triphenyl-1H-1,2,3-benzotriphosphole and related compounds. Part II , 1972 .

[64]  P. M. Garrett,et al.  Preparation and characterization of the (3)-1,2- and (3)-1,7-dicarbadodecahydroundecaborate(-1) ions , 1968 .

[65]  J. Daly The crystal and molecular structure of 1,2,3-triphenyl-1,2,3-triphosphaindane , 1966 .

[66]  M. Pragnell,et al.  The synthesis, structure, and reactions of 1,2,3-triphenyl-1,2,3-triphosphaindane, a novel heterocyclic system. A new synthesis of the 5,10-dihydrophosphanthren system , 1966 .

[67]  P. M. Garrett,et al.  The Thermal Isomerization of C-Phenyldicarbaundecaborate(12) , 1964 .

[68]  M. Hawthorne,et al.  Dicarbaundecaborane(13) and Derivatives , 1964 .

[69]  J. Daly 1179. The crystal and molecular structure of phosphobenzene A, (PC6H5)5 , 1964 .

[70]  R. Alexander,et al.  CHEMISTRY OF DECABORANE-PHOSPHORUS COMPOUNDS. IV. MONOMERIC, OLIGOMERIC AND CYCLIC PHOSPHINO CARBORANES , 1963 .

[71]  K. Ǐssleib,et al.  Tetracyclohexyl-cyclotetraphosphin und Cyclohexyl-halogenphosphine , 1960 .