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In chemistry, phosphine-boranes are organophosphorus compounds with the formula R3−nHnPBH3. They are Lewis acid-Lewis base adducts derived from organophosphines
Phosphine-borane
Chemical compound
Phosphine-boranes, with the formula R3−nHnPBH3, are adducts of organophosphines and borane. Borane adducts with amines are more widely used. Borane makes
Borane
Chemical compound hydrogen phosphide
Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Pure
Phosphine
Class of chemical compounds
ClAg(PPh3)2 The adducts formed from phosphines and borane are useful reagents. These phosphine-boranes are air-stable, but the borane protecting group can be removed
Organophosphine
Chemical compound
secondary boranes are less common. Tert-butylamine borane (tBuNH2→BH3) Phosphine-borane (R3P→BH3) Borane dimethylsulfide ((CH3)2S→BH3) Borane–tetrahydrofuran
Ammonia_borane
Chemical compound
Tris(pentafluorophenyl)borane is a key reagent leading to the concept of frustrated Lewis pairs. The combination of BCF and bulky basic phosphines, such as tricyclohexylphosphine
Tris(pentafluorophenyl)borane
Chemical compound
treating cobalt(II) chloride with the phosphine. The phosphine-borane H3BPMePh2 prepared by treating the phosphine with borane. Denniston, Michael L.; Martin
Methyldiphenylphosphine
Organic compound with at least one covalent carbon–phosphorus bond
of organophosphines causes trouble, they can be protected as phosphine-boranes. Phosphines are also reducing agents, as illustrated in the Staudinger reduction
Organophosphorus_chemistry
Chemical reaction between molecular hydrogen and another compound or element
state. Another system for metal-free hydrogenation is based on the phosphine-borane, compound 1, which has been called a frustrated Lewis pair. It reversibly
Hydrogenation
Technique for measuring a molecule's Lewis acidity
of "frustrated Lewis pairs": facile formation of phosphine-boranes and cationic phosphonium-boranes", Dalton Trans., 2007, 3407–3414. doi: 10.1039/b704417h
Gutmann–Beckett_method
Polymer whose backbone does not contain carbon
S. Weller (2015). "The Catalytic Dehydrocoupling of Amine–Boranes and Phosphine–Boranes". Synthesis and Application of Organoboron Compounds. Topics
Inorganic_polymer
Molecule with a hydrogen bound to a more electropositive element or group
synthesis; also borane, pentaborane and decaborane arsine: used for doping semiconductors stibine: used in semiconductor industry phosphine: used for fumigation
Hydride
Class of chemical compounds
can reduce phosphine oxides and generally give higher yields: R3PO + Si2Cl6 → R3P + Si2OCl6 2 R3PO + Si3Cl8 → 2 R3P + Si3O2Cl8 Boranes and alanes also
Phosphine_oxides
Chemical compound
use of the diphenylphosphine–borane complex, Ph2PH•BH3 avoids the problem of phosphine oxidation by protecting the phosphine from oxidation and is available
Diphenylphosphine
Main-group allene analog
1:1 molar ratio of phosphaallene to H3B(SMe2) yielded a di(phosphaalkenyl)borane, and the reaction in 2:1 molar ratio of phosphaallene to H3B(SMe2) yielded
1-Phosphaallenes
metal-free H2 activation and hydrogenation catalysts. Unlike the neutral boranes typically used in frustrated Lewis pair (FLP) chemistry of this type, borenium
Boranylium_ions
Chemical catalyst
intermolecular (Scheme 1) and intramolecular (Scheme 2) FLP consisting of a phosphine and a borane were used to selectively capture and release carbon dioxide. When
Frustrated_Lewis_pair
Chemistry laboratory technique
halogenated compounds and especially strongly coordinating species such as phosphines and thiols can be problematic because they irreversibly poison the copper
Air-free_technique
Radicals centered on boron atoms
organic reactivities. While the first studies of boryl radicals involved borane radical anions, the study of overall neutral boryl radical species was unlocked
Boryl_radicals
Molecule made of a main-group element bound to hydrogen
unstable. Group III parent hydrides exist only under extraordinary conditions. Borane dimerizes irreversibly. Gallane and heavier congeners polymerize, sometimes
Parent_hydride
Formalism used for classifying compounds
transition metals and main group elements and mixtures thereof, such as boranes. Atoms are called "electron-deficient" when they have too few electrons
Electron_counting
Type of organosulfur compound
synthon. A frustrated Lewis pair, such as tris(tert-butyl) phosphine and tris(pentafluorophenyl)borane, can attach to the NSO chain to yield a R'3P=N+(R)SOB−R"3
Sulfinylamine
Chemical theory about acids and bases
theory: Bulk metals are soft acids and are poisoned by soft bases such as phosphines and sulfides. Hard solvents such as hydrogen fluoride, water and the protic
HSAB_theory
catecholborane (HBcat) or 4,4,6-trimethyl-1,3,2-dioxaborinane. These two borane compounds are otherwise slow to participate in hydroboration. In 1985, Männig
Metal-catalysed_hydroboration
Chemical compound with hydrogen and pnictogen atoms
resembling urine or fish, commonly the result of the decomposition of urea. Phosphine, arsine, and stibine smell like fish or garlic. Dipnictogen tetrahydrides
Pnictogen_hydride
Catalyzed organic reactions that produce an organoboron compound
ligands, including tris(3,5-bis(trifluoromethyl)phenyl)phosphine and an immobilized phosphine, replace dtbpy. Likewise, it occurs when certain bidentate-but-hemilabile
Borylation
Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')
For instance, diethyl ether forms a complex with boron trifluoride, i.e. borane diethyl etherate (BF3·O(CH2CH3)2). Ethers also coordinate to the Mg center
Ether
Type of saturated hydrocarbon compound
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Alkane
Chemical compound
doi:10.1002/zaac.19251470115. Rathke, Michael W.; Millard, Alan A. (1978). "Boranes in functionalization of olefins to amines: 3-Pinanamine (Bicyclo[3.1.1]heptan-3-amine
Hydroxylamine-O-sulfonic_acid
Class of chemical compounds
system [Pd(Me-DuPhos(MeCN)2)](BF4)2 Mono oxidation of (R,R)-Me-Duphos using borane dimethylsulfide as protective group and hydrogen peroxide as oxidizing agent
DuPhos
Chemical compound
phosphorus hydrides. It is the impurity that typically causes samples of phosphine to ignite in air. Diphosphane adopts the gauche conformation (like hydrazine
Diphosphane
Class of positively-charged molecules
negative anion. boronium cation, BH+4 (protonated borane) further boronium cations, B xH+ y (protonated boranes) Carbonium ions (protonated hydrocarbons) have
Onium_ion
Chemist and university president
production and properties of phosphines. She also worked on borohydrides, phosphite, metal-phosphorus compounds, aryl phosphines Morse also led the professional
Karen_Morse_(chemist)
Robertson, A. P. M.; Sloan, M. E.; Manners, I. (2010). "Amine− and Phosphine−Borane Adducts: New Interest in Old Molecules". Chem. Rev. 110 (7): 4023–4078
Transition metal boryl complex
Transition_metal_boryl_complex
Tridentate ligand which "pinches" the central metal atom
other scorpionate ligands are known. For example, the Tm and tripodal phosphine classes have an equally good claim to be scorpionate ligands. Many of
Scorpionate_ligand
Class of aluminium compounds
are observed when mixing dialumene with common inorganic molecules. Amino borane, a competitive candidate for hydrogen storage, can interact with catalytic
Dialumene
Chemical compound
reactivity can occasionally differ. With the Lewis acid tris(pentafluorophenyl)borane, the expected acid/base adduct forms, however, over long periods of time
N-Heterocyclic_silylene
Class of organic compounds
or, in rare cases, halides or NR2 groups. NPR3− is isoelectronic with phosphine oxides (OPR3) and siloxides ([OSiR3]−), but far more basic. By varying
Phosphinimide_ligands
Chemical bond theory
simpler case is the formation of adducts of borane. Monomeric BH3 does not exist appreciably, so the adducts of borane are generated by degradation of diborane:
Lewis_acids_and_bases
telluride – Bi2Te3 Bismuth tribromide – BiBr3 Bismuth tungstate – Bi2WO6 Borane – BH3 Borax – Na2B4O7·10H2O Borazine – B3H6N3 Borazocine ((3Z,5Z,7Z)-azaborocine)
List_of_inorganic_compounds
The following is a partial list of the "D" codes for Medical Subject Headings (MeSH), as defined by the United States National Library of Medicine (NLM)
List_of_MeSH_codes_(D01)
Class of chemical compounds
addition. Nontrigonal phosphorus compounds can also react with ammonia–borane to form a formal dihydrogen oxidative addition product. This compound proved
Nontrigonal pnictogen compounds
Nontrigonal_pnictogen_compounds
Owen, Gareth R. (2010-12-06). "Double addition of H2 to transition metal–borane complexes: a 'hydride shuttle' process between boron and transition metal
Metal-ligand_cooperativity
Chemical compound
vinylcyclohexene. Approximately 10,000 tons were produced in 2005. COD reacts with borane to give 9-borabicyclo[3.3.1]nonane, commonly known as 9-BBN, a reagent in
1,5-Cyclooctadiene
Hydrocarbon compound (H2C=CH2)
Phosphodiester Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Arsenic
Ethylene
Chemical compound
framework. Similarly, a photochemical approach utilizing tris(triphenylsilyl)borane as a precursor has been reported, wherein a highly reactive silylborylene
Borirene
Chemical compound
and awkward preparation contrast with the more conventional fumigant phosphine. As stibine (SbH3) is similar to arsine (AsH3); it is also detected by
Stibine
Organophosphorus compound with a phosphorus–phosphorus double bond
Verbindungen, XVI. Wege zur Darstellung primärer, sekundärer und tertiärer Phosphine". Chemische Berichte (in German). 91 (8): 1583–1588. doi:10.1002/cber
Diphosphenes
NMR via protons, hydrogen-1 nuclei
(2006-04-01). "High Atom-Economical One-Pot Synthesis of Secondary Phosphines and Their Borane Complexes Using Recycling Phosphorus Donor Reagent". Organic
Proton nuclear magnetic resonance
Proton_nuclear_magnetic_resonance
Chemical compound (SiH4)
Iwasaka, M. & Kaise, M. (1995). "Spontaneous Ignition Limits of Silane and Phosphine". Combustion and Flame. 101 (1–2): 170–174. Bibcode:1995CoFl..101..170K
Silane
Chemical element with atomic number 5 (B)
phenomenon, see phosphine). The boranes are also highly flammable and require special care when handling. Some combinations of boranes and other compounds
Boron
Chemical compound
diphosphine is often the spontaneously pyrophoric contaminant in samples of phosphine). It also arises by thermal decomposition disilane via both photochemical
Disilane
Chemical compound
compounds Ammonia Hydrazine Diazene Triazene Tetrazene Pentazole Hexazine Phosphine Diphosphane Triphosphane Diphosphene Hexaphosphabenzene Arsine Diarsane
Triazane
bond activation. For example, C-F activation of tris(pentafluorophenyl)borane by NHC-stabilized phosphaboranes, [(tmp)(L)B=PMes*] (L = IMe4), was reported
Group_13/15_multiple_bonds
Related chemical elements of the periodic table
capable of forming many compounds with hydrogen, sometimes called boranes. The simplest borane is diborane, or B2H6. Another example is B10H14. The next group-13
Boron_group
Laboratory device for preparing gases
magnesium germanide Stannanes from stannides, e.g. magnesium stannide Boranes from borides (e.g. tetraborane from magnesium boride, aluminium boride
Kipp's_apparatus
Chemical reaction used in organic synthesis
(Pd(OAc)2, PdCl2(MeCN)2, PdCl2(PPh3)2, BnPdCl(PPh3)2, etc.) by added phosphine ligands or organotin reagents is also common Oxidative addition to the
Stille_reaction
Chemical compound
IDLH (Immediate danger) 3 ppm Related compounds Related hydrides Ammonia Phosphine Stibine Bismuthine Related compounds Hydrogen selenide Supplementary data
Arsine
Heterocyclic aromatic organic compound
a sulfation agent used to convert alcohols to sulfate esters. Pyridine-borane (C5H5NBH3, melting point 10–11 °C) is a mild reducing agent. Transition
Pyridine
Mahler, Walter (August 1957). "A New Synthesis of Bis-Trifluoromethyl-Phosphine, (CF3)2PH". Journal of the American Chemical Society. 79 (15): 4242. doi:10
List_of_gases
Systematic naming of chemical compounds
the base name ending with -ane, e.g. borane (BH3), oxidane (H2O), phosphane (PH3) (Although the name phosphine is also in common use, it is not recommended
Chemical_nomenclature
Poisonous and flammable gas
telluride Hydrogen polonide Hydrogen disulfide Sulfanyl Related compounds Phosphine Except where otherwise noted, data are given for materials in their standard
Hydrogen_sulfide
2005 edition of the Nomenclature of Inorganic Chemistry
the main group elements (groups 13–17) are given -ane base names, e.g. borane, BH3. Acceptable alternative names for some of the parent hydrides are water
IUPAC nomenclature of inorganic chemistry 2005
IUPAC_nomenclature_of_inorganic_chemistry_2005
Hydrocarbon compound containing one or more C=C bonds
cycloaddition with an alkyne and CO Hydroboration–oxidation alcohols reagents: borane, then a peroxide Oxymercuration-reduction alcohols electrophilic addition
Alkene
Hydrocarbon compound containing one or more C≡C bonds
across C≡C is general for silanes, boranes, and related hydrides. The hydroboration of alkynes gives vinylic boranes which oxidize to the corresponding
Alkyne
Hydrocarbon compound (HC≡CH)
usually have a marked odor due to impurities such as divinyl sulfide and phosphine. As an alkyne, acetylene is unsaturated because its two carbon atoms are
Acetylene
Chemical compound
5 kJ/mol; for comparison, water's is 40.65 kJ/mol, methane 8.19 kJ/mol and phosphine 14.6 kJ/mol) and can be transported in pressurised or refrigerated vessels;
Ammonia
Chemical compound
Stable hydrogen-bonded adducts with various amine oxides and substituted phosphine oxides are known. The adduct with triphenylphosphine oxide can serve as
Hydrogen_peroxide
Class of diboron compounds
B2Cl4 and either SH2 or PH3, and adducts formed by B2Cl4 or B2F4 and weak phosphine donors such as PCl3 or PBr3. There are, however, some adducts that are
Tetrahalodiboranes
Overview of and topical guide to organic chemistry
Polyphosphates Phosphazenes Iminophosphoranes Polyphosphazenes Phosphinates Phosphines Diphosphines Phosphinites Phosphites Phosphoramidites Phosphonates Phosphonites
Outline_of_organic_chemistry
Chemical compound
BF does react with arsine, carbon monoxide, phosphorus trifluoride, phosphine, and phosphorus trichloride to make adducts like (BF2)3B•AsH3, (BF2)3B•CO
Boron_monofluoride
Chemical compound
+ 4 H2O Hydrogen(•) is obtained in situ from the homolysis of water. Phosphine- and NHC-copper hydride species have been developed as reagents in organic
Copper_hydride
Chemical compound
ISBN 978-0-08-037941-8. Marianne Baudler, Klaus Glinka (1993). "Monocyclic and Polycyclic Phosphines". Chem. Rev. 93: 1623–1667. doi:10.1021/cr00020a010. IUPAC CHEBI
Triphosphane
Chemical compound
stable than nitrogen pentahydride but still unstable to decomposition to phosphine and hydrogen gas. Its organic derivatives (phosphoranes) are more stable
Nitrogen_pentahydride
Chemical compound
Phosphine reduction using aluminium hydride
Aluminium_hydride
bidirectional properties, this compound has the characteristic that it carries two borane protected cyanide ligands at the iron atom. Some works about bio-mimetic
Hydrogenase_mimic
Chemical compound
borate. As a strong Lewis acid, BCl3 forms adducts with tertiary amines, phosphines, ethers, thioethers, and halide ions. Adduct formation is often accompanied
Boron_trichloride
Chemical compound
numbers. Also whilst N donor ligands form stronger bonds to alumane than phosphines the reverse is typically true for gallane. The monomeric structure of
Gallane
10294–34–5 BF3 boron trifluoride 7637–07–2 BH3 borane 13283-31-3 BH4− borohydride ion 16971-29-2 BH6N ammonia borane 13774-81-7 BI3 boron triiodide 13517–10–7
Glossary_of_chemical_formulae
Chemical compound of bismuth and hydrogen
Molecular shape trigonal pyramidal Related compounds Related hydrides Ammonia Phosphine Arsine Stibine Related compounds Polonium hydride Except where otherwise
Bismuthine
The following is a partial list of the "D" codes for Medical Subject Headings (MeSH), as defined by the United States National Library of Medicine (NLM)
List_of_MeSH_codes_(D02)
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PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
PHOSPHINE BORANE
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