Synthesis of Carbon-Phosphorus Bonds

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Publisher : CRC Press
ISBN 13 : 0203998243
Total Pages : 200 pages
Book Rating : 4.2/5 (39 download)

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Book Synopsis Synthesis of Carbon-Phosphorus Bonds by : Robert Engel

Download or read book Synthesis of Carbon-Phosphorus Bonds written by Robert Engel and published by CRC Press. This book was released on 2003-12-18 with total page 200 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis of Carbon-Phosphorus Bonds, Second Edition is a working guide for the laboratory, incorporating classical approaches with the recent developments of carbon-phosphorus (C-P) bond formation. These advances include the preparation of phosphoranes - specifically in the use of transient oxophosphoranes as intermediates in organophosphorus comp

Synthesis of Carbon-Phosphorus Bonds, Second Edition

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Author :
Publisher : CRC Press
ISBN 13 : 9781135502034
Total Pages : 200 pages
Book Rating : 4.5/5 (2 download)

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Book Synopsis Synthesis of Carbon-Phosphorus Bonds, Second Edition by : Robert Engel

Download or read book Synthesis of Carbon-Phosphorus Bonds, Second Edition written by Robert Engel and published by CRC Press. This book was released on 2003-12-18 with total page 200 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis of Carbon-Phosphorus Bonds, Second Edition is a working guide for the laboratory, incorporating classical approaches with the recent developments of carbon-phosphorus (C-P) bond formation. These advances include the preparation of phosphoranes - specifically in the use of transient oxophosphoranes as intermediates in organophosphorus compound synthesis ñ along with the new approaches towards the preparation of compounds with aromatic and vinylic C-P bonds. Synthesis of Carbon-Phosphorus Bonds, Second Edition serves as a useful tool in the laboratory. It offers detailed surveys of IUPAC nomenclature recommendations, common notation systems, and various experimental examples. These features help to make this text an effective source of critical and annotated references, as well as a a working guide for organic and phosphorus chemists specifically, or for any chemists working with C-P bonds.

Carbon-phosphorus Bond Formation

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ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (328 download)

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Book Synopsis Carbon-phosphorus Bond Formation by : Yamina Belabassi

Download or read book Carbon-phosphorus Bond Formation written by Yamina Belabassi and published by . This book was released on 2009 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The work presented in this dissertation deals with the development of new methodologies for P-C bond formation as well as synthesizing biologically relevant organophosphorus compounds. A distinct emphasis is given to the important synthetic targets, the H-phosphinates. A review of relevant literature is provided in Chapter 1. Chapter 2 describes the synthesis and structural analyses, of triphenylmethyl-containing phosphorus compounds. For the first time, both phosphonothioic and boranophosphonic acids have been characterized by single X-ray diffractometry. The third chapter details the preparation and the reactivity of phosphine-borane complexes. Novel dialkoxyphosphine-borane complexes were introduced, both as general synthetic intermediates for the preparation of H-phosphinates or disubstituted phosphinic acids, and as boranophosphonate precursors. Related to this chemistry, silylation of an H-phosphinate intermediate can also be conducted and the resulting phosphonite protected with borane. This allows the temporary protection of the sensitive P-H group, so that manipulations of the alkyl chain might be conducted. In chapter 4, the palladium-catalyzed cross-coupling reaction of dialkylphosphites with aryl and heteroaryl halides is presented. An efficient, versatile and economically attractive alternative to the original Hirao cross-coupling by using only 1 mol% (or less) Pd(OAc)2/dppf is described. Moreover, first example of palladium-catalyzed P-C bond formation between activated aryl chlorides and a phosphite are herein reported. Chapter 5 focuses on the free-radical hydrophosphinylation of alkynes. The triethylborane-initiated radical addition of sodium hypophosphite to terminal alkyne affords the previously unknown 1,1-bis-H-phosphinates, precursors of the biologically relevant 1,1-bisphosphonates (e.g., treatment of bone diseases). Thus, the oxidative conversion of 1,1-bis-H-phosphinates to the corresponding bisphosphonates, as well as the synthesis of a series of bio-conjugates (steroids, carbohydrates, fluoroquinolones) was investigated. In the last chapter, the palladium-catalyzed hydrophosphinylation of hypophosphorous acid derivatives to terminal alkynes is reported. In an effort to improve the regioselectivity of the reaction, various terminal alkynes were tested, as well as the solvent and catalyst system.

Carbon-phosphorus and Oxygen-phosphorus Bond Formation

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ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (899 download)

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Book Synopsis Carbon-phosphorus and Oxygen-phosphorus Bond Formation by : Henry C. Fisher

Download or read book Carbon-phosphorus and Oxygen-phosphorus Bond Formation written by Henry C. Fisher and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The work in this dissertation deals with the continued development of new methodologies for P-C and P-O bond formation using alternative methods that avoid the use of PCl3. A review of the relevant literature that proceeds this work is presented in Chapter 1. Chapter 2 describes the study of the P(III) to P(V) tautomerization of phosphinylidene compounds and the structural influences that effect the thermodynamic and kinetic properties to favor the more reactive P(III) species. A collaboration using both computational and experimental methods, show that electron withdrawing groups such as phenyl stabilize the tautomerization of phosphinylidene compounds. The second part of this work highlights the influence of various catalysts on P(III) to P(V) tautomerization. Using computational chemistry as a screening tool, a variety of organic acids and bases were tested. The calculations and experimental results are in good agreement. Chapter 3 describes the work to develop the nickel-catalzyed hydrophosphinylation of unactivated alkenes, an extension of the work started with the nickel-catalyzed hydrophosphosphinylation of alkynes. The results show that nickel chloride is pre-activated to an active Ni(0) species and can be stabilized by the inexpensive bisphosphine ligand, ethylbis(diphenylphosphine), dppe. The reaction occurs at room temperature and works on a variety of different alkene substrates. Other manipulations used in tandem with the initial nickel hydrophosphinylation are highlighted, and show the reaction to be a versatile tool for making alkyl-H-phosphinate derivatives as precursors for further use. Chapter 4 details the development of manganese-promoted intermolecular and intramolecular additions of alkenes, alkynes and aryl compounds with H-phosphinates is described. The system utilizing catalytic Mn(OAc)2 either neat or in DMSO, is successful for a variety of different alkenes and two alkyne substrates. A more efficient and cost-effective system was recently developed for H-phosphinate arylations using catalytic Mn(OAc)2 and MnO2 as an oxidant, and further applied to alkene phosphonochlorination with LiCl. In Chapter 5, nickel-catalyzed oxidation of alkyl hypophosphites is utilized to prepare ubiquitous alkyl-H-phosphonates starting from hypophosphorous acid and avoiding the use of PCl3. The reaction can be considered a form of water splitting. The studies show that after the intitial esterification step, NiCl2 or Ni/SiO2 is enough to oxidize the first P-H bond to form the desired phosphonate. The reaction has been applied to the synthesis of the global herbicide glyphosate.

New Reactions and Reagents for Phosphorus-carbon Bond-formation

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Publisher :
ISBN 13 :
Total Pages : 373 pages
Book Rating : 4.:/5 (119 download)

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Book Synopsis New Reactions and Reagents for Phosphorus-carbon Bond-formation by : Michael B. Geeson

Download or read book New Reactions and Reagents for Phosphorus-carbon Bond-formation written by Michael B. Geeson and published by . This book was released on 2020 with total page 373 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1 takes the format of an "Outlook", and sets forth the case for developing sustainable methods in the synthesis of phosphorus-containing compounds. Methods used by nature for phosphorus-carbon bond-formation, or in the chemistry of other elements such as silicon, are discussed as model processes for the future of phosphorus in chemical synthesis. Chapter 2 describes the discovery of [TBA][P(SiCl3)2], prepared from [TBA]3[P3O9]-.2H2O and trichlorosilane. The bis(trichlorosilyl)phosphide anion is used to prepare compounds that contain P–C, P–O, P–F, and P–H bonds in a method that bypasses white phosphorus (P4), the traditional route to organophosphorus compounds. Chapter 3 extends the phosphate precursors to [TBA][P(SiCl3)2] from trimetaphosphate to crystalline phosphoric acid. Balanced equations are developed for the formation of [TBA][P(SiCl3)2] from phosphate sources and the byproducts are identified as hexachlorodisiloxane and hydrogen gas. Extension of trichlorosilane reduction to bisulfate provides improved access the known trichlorosilylsulfide anion, [TBA][SSiCl3]. This anion was used as a thionation reagent to prepare thiobenzophenone and benzyl mercaptan from benzophenone and benzyl bromide, respectively. Chapter 4 describes the synthesis of neutral phosphine, HP(SiCl3)2, obtained by protonation of [TBA]1 with triflic acid. HP(SiCl3)2 is a highly efficient reagent for photochemical hydrophosphination of terminal alkenes. The phosphorus-silicon bonds in the hydrophosphination products can be functionalized to provide compounds of the general formulae: RPCl2, RPH2, [RP(R')3]Cl, RP(O)(H)(OH), and RP(O)(OH)2. Chapter 5 describes a method to prepare phosphiranes (three-membered rings that contain a phosphorus atom) from anthracene-based phosphinidene precursors and styrenic olefins. The phosphinidene transfer reaction requires an organoiron and fluoride catalyst. The resulting phosphirane is prepared in good yield (73%) with high stereoselectivity (>99%). Experimental investigations into the mechanism point toward the intermediacy of an iron-coordinated fluorophosphide species.

Carbon-carbon Bond Formation

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Publisher : CRC Press
ISBN 13 : 9780824767877
Total Pages : 480 pages
Book Rating : 4.7/5 (678 download)

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Book Synopsis Carbon-carbon Bond Formation by : Robert L. Augustine

Download or read book Carbon-carbon Bond Formation written by Robert L. Augustine and published by CRC Press. This book was released on 1979-04-01 with total page 480 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Carbon-Carbon ?-Bond Formation

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Publisher : Elsevier
ISBN 13 : 008091246X
Total Pages : 1209 pages
Book Rating : 4.0/5 (89 download)

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Book Synopsis Carbon-Carbon ?-Bond Formation by : G. Pattenden

Download or read book Carbon-Carbon ?-Bond Formation written by G. Pattenden and published by Elsevier. This book was released on 1992-09-08 with total page 1209 pages. Available in PDF, EPUB and Kindle. Book excerpt: Volume 3 covers carbon-to-carbon single bond forming reactions involving sp3, sp2 and sp carbon centers, but only those which do not involve additions to C-X &pgr;-bonds. The volume first compares and contrasts the alkylation reactions of all types of sp3 carbon nucleophiles and also covers vinyl and alkynyl carbanions. Following on from Volume 2, a separate section covers Friedel-Crafts alkylation reactions, which is complemented by discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions leading to &agr;-bond formation, and involving all types of combinations ofsp3, sp2 and sp carbon centers are next covered, including those reactions based on pinacol, acyloin and phenol oxidative coupling reactions, and also the Kolbe reaction. Rearrangement reactions, leading to carbon-to-carbon &agr;-bond formation, are often used in a clever manner in synthesis. The volume includes all those rearrangement reactions based on intermediate carbonium ions and carbanions, and also includes the benzil-benzilic acid and the Wolff rearrangements. The volume closes with coverage of carbonylation reactions, and the use of carbene insertion reactions into the C-H bond in synthesis.

METHODOLOGY AND SYNTHESIS USING HYPOPHOSPHOROUS DERIVATIVES: PHOSPHORUS-CARBON BOND FORMATION AND GABA ANALOGUES.

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ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (631 download)

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Book Synopsis METHODOLOGY AND SYNTHESIS USING HYPOPHOSPHOROUS DERIVATIVES: PHOSPHORUS-CARBON BOND FORMATION AND GABA ANALOGUES. by :

Download or read book METHODOLOGY AND SYNTHESIS USING HYPOPHOSPHOROUS DERIVATIVES: PHOSPHORUS-CARBON BOND FORMATION AND GABA ANALOGUES. written by and published by . This book was released on 2006 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The focus of this work lies on the exploitation of hypophosphorous derivatives in order to develop new methodologies for P-C bond formation as well as synthesizing biologically relevant phosphorus compounds. A review of the work published to date from the Montchamp group is provided in Chapter 1: Much of the methodology is applied in the remainder of the thesis in reactions such as radical addition, base-promoted alkylation and cross-coupling of anilinium hypophosphite. The following chapter describes initial results of the transition-metal catalyzed cross-coupling in the presence of beta-hydrogens and with chloromethylphthalimide. The application of phosphine-borane chemistry as a phosphinylidene protecting group is discussed in Chapter 3. An in-depth literature review provides the background for the new methodology. Novel gamma-aminobutyric acid analogues are synthesized using methods developed within the Montchamp group. Their synthesis and biological evaluation are discussed in the final chapter.

Reactivity of P-H Group of Phosphorus Based Compounds

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Publisher : Academic Press
ISBN 13 : 0128138351
Total Pages : 465 pages
Book Rating : 4.1/5 (281 download)

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Book Synopsis Reactivity of P-H Group of Phosphorus Based Compounds by : Kolio D. Troev

Download or read book Reactivity of P-H Group of Phosphorus Based Compounds written by Kolio D. Troev and published by Academic Press. This book was released on 2017-09-06 with total page 465 pages. Available in PDF, EPUB and Kindle. Book excerpt: Reactivity of P-H Group of Phosphorus Based Compounds bridges the gap between inorganic and organic phosphorus compounds, providing a basis to explore the myriad possibilities for synthesis of novel low and high molecular phosphorus-containing compounds. It covers well-documented reactions in detail, including: tautomerization, oxidation, reduction, alkylation, oxidation coupling, addition reaction to: carbon-carbon multiple bonds, Schiff base, isocyanates, nitriles, epoxides; addition to carbonyl group, Kabachnik- Fields reaction, cross-coupling reaction and more. In an accessible style complete with synthetic routes and figures, the resource then covers the reactivity of multiple P-H group members: phosphines, phosphine oxides, hypophosphorus acid, H-phosphinic acids and polys(alkylene H-phosphonate). This valuable coverage supports the advancement of research and applications in this area for scientists solving a scientific problem or starting a variety of new projects, such as a new reaction for the synthesis of biologically active compounds, new methods of polymer synthesis or a new methodology for polymer modification. Describes the diverse reactivity of the phosphorus-hydrogen group, perhaps the most powerful in organic chemistry Includes practical information for the synthesis of catalysts, biologically active substances, flame retardants, advance materials and polymer materials Offers a visually-accessible guide to important reactions by an internationally recognized chemist

Phosphorus-carbon Bond Formation

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Publisher :
ISBN 13 :
Total Pages : 474 pages
Book Rating : 4.:/5 (56 download)

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Book Synopsis Phosphorus-carbon Bond Formation by : Sylvine Deprele

Download or read book Phosphorus-carbon Bond Formation written by Sylvine Deprele and published by . This book was released on 2004 with total page 474 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Synthesis, Characterization and Reactions of Complexes Containing New Ligands with Carbon-phosphorus Multiple Bonds

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Publisher :
ISBN 13 :
Total Pages : 304 pages
Book Rating : 4.:/5 (393 download)

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Book Synopsis Synthesis, Characterization and Reactions of Complexes Containing New Ligands with Carbon-phosphorus Multiple Bonds by : Wayde Vincent Konze

Download or read book Synthesis, Characterization and Reactions of Complexes Containing New Ligands with Carbon-phosphorus Multiple Bonds written by Wayde Vincent Konze and published by . This book was released on 1997 with total page 304 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Carbon-carbon bond formation

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ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (473 download)

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Book Synopsis Carbon-carbon bond formation by : Robert L. Augustine

Download or read book Carbon-carbon bond formation written by Robert L. Augustine and published by . This book was released on 1979 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:

Comprehensive Organic Functional Group Transformations

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Publisher : Elsevier
ISBN 13 : 9780080423258
Total Pages : 1380 pages
Book Rating : 4.4/5 (232 download)

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Book Synopsis Comprehensive Organic Functional Group Transformations by : Alan R. Katritzky

Download or read book Comprehensive Organic Functional Group Transformations written by Alan R. Katritzky and published by Elsevier. This book was released on 2003-03-21 with total page 1380 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this Volume, containing 24 chapters devoted to carbon attached by single bonds to two heteroatoms, the reader will find several chapters reviewing the synthesis of familiar functional groups, notably acetals, dithioacetals, aminals and the various mixed species. The derivatives with tetracoordinated (saturated) carbon are described in Part I and those, eg. ketene acetals, of tricoordinated carbon in Part II. However, the treatment is comprehensive and the authors have uncovered much fascinating chemistry concerning less familiar groups, including some like geminal halohydrins, halo amines and diols that are often unstable. Again, a surprisingly large number of compounds having two metals attached to the same carbon have been located in the literature, and the abundance of phosphorus derivatives, eg. those with geminal nitrogen functions, reflects their importance as biologically active species and as intermediates in synthesis. Part III consists of a single, short chapter describing dicoordinate carbon (carbenes) and examples of carbon cations, anions and radicals. Here the treatment is deliberately selective since throughout the work as a whole emphasis is placed on the synthesis of isolable species rather than the transient intermediates of organic reactions.

Organophosphorus Chemistry

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Publisher : John Wiley & Sons
ISBN 13 : 3527335722
Total Pages : 586 pages
Book Rating : 4.5/5 (273 download)

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Book Synopsis Organophosphorus Chemistry by : Viktor Iaroshenko

Download or read book Organophosphorus Chemistry written by Viktor Iaroshenko and published by John Wiley & Sons. This book was released on 2019-04-22 with total page 586 pages. Available in PDF, EPUB and Kindle. Book excerpt: Filling the gap for an up-to-date reference that presents the field of organophosphorus chemistry in a comprehensive and clearly structured way, this one-stop source covers the chemistry, properties, and applications from life science and medicine. Divided into two parts, the first presents the chemistry of various phosphorus-containing compounds and their synthesis, including ylides, acids, and heterocycles. The second part then goes on to look at applications in life science and bioorganic chemistry. Last but not least, such important practical aspects as 31P-NMR and protecting strategies for these compounds are presented. For organic, bioinorganic, and medicinal chemists, as well as those working on organometallics, and for materials scientists. The book, a contributed work, features a team of renowned scientists from around the world whose expertise spans the many aspects of modern organophosphorus chemistry.

Room Temperature Organic Synthesis

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Publisher : Elsevier
ISBN 13 : 0128011386
Total Pages : 388 pages
Book Rating : 4.1/5 (28 download)

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Book Synopsis Room Temperature Organic Synthesis by : Goutam Brahmachari

Download or read book Room Temperature Organic Synthesis written by Goutam Brahmachari and published by Elsevier. This book was released on 2015-03-19 with total page 388 pages. Available in PDF, EPUB and Kindle. Book excerpt: Filling a gap in the scientific literature, Room Temperature Organic Synthesis is unique in its authoritative, thorough, and applied coverage of a wide variety of "green" organic synthetic methodologies. The book describes practical, feasible protocols for room temperature reactions to produce carbon-carbon and carbon-heteroatom bond formations including aliphatic, aromatic, alicyclic, heterocycles, and more. Consistently organized for easy access, each selected reaction is discussed in a very compact and structured manner including: reaction type, reaction condition, reaction strategy, catalyst, keywords, general reaction scheme, mechanism (in selected cases), representative entries, experimental procedure, characterization data of representative entries, and references. This book will be a valuable resource for synthetic organic, natural products, medicinal, and biochemists as well as those working in the pharmaceutical and agrochemical industry. Includes more than 300 protocols for a green approach to organic synthesis Provides specific detail about experimental conditions Increases efficiency in the laboratory by eliminating time-consuming literature searches

Chemistry and Application of H-Phosphonates

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Publisher : Elsevier
ISBN 13 : 008047649X
Total Pages : 308 pages
Book Rating : 4.0/5 (84 download)

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Book Synopsis Chemistry and Application of H-Phosphonates by : Kolio D. Troev

Download or read book Chemistry and Application of H-Phosphonates written by Kolio D. Troev and published by Elsevier. This book was released on 2006-09-25 with total page 308 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chemistry and Application of H-Phosphonates is an excellent source for those planning the synthesis of new phosphorus-containing compounds and in particular derivatives containing a phosphonate, phosphoramide or phosphonic acid diester group. The rich chemistry, low cost and easy availability of diesters of H-phosphonic acid makes them an excellent choice as synthone in a number of practically important reactions. Phosphonic acid esters are intermediates in the synthesis of important classes of compounds such as alpha-aminophosphonic acids, bisphosphonates, epoxyalkylphosphonates, alpha-hydroxyalkylphosphonates, phosphoramides, poly(alkylene H-phosphonate)s, poly(alkylene phosphate)s, nucleoside H-phosphonates. The synthesis of each of these compound classes is reviewed in detail. Alpha-Aminophosphonic acids are an important class of biologically active compounds, which have received an increasing amount of attention because they are considered to be structural analogues of the corresponding Alpha-amino acids. The utilities of alpha-aminophosphonates as peptide mimics, haptens of catalytic antibodies, enzyme inhibitors, inhibitors of cancers, tumours, viruses, antibiotics and pharmacologic agents are well documented. Alpha-Hydroxyalkanephosphonates are compounds of significant biological and medicinal applications. Dialkyl epoxyalkylphosphonates are of interest because of their use as intermediates in the synthesis of bioactive substances, and as modifiers of natural and synthetic polymers. Bisphosphonates are drugs that have been widely used in different bone diseases, and have recently been used successfully against many parasites. Poly(alkylene H-phosphonate)s and poly(alkylene phosphate)s are promising, biodegradable, water soluble, new polymer-carriers of drugs. Nucleoside H-phosphonates seem to be the most attractive candidates as starting materials in the chemical synthesis of DNA and RNA fragments. The 5’-hydrogen phosphonate-3’-azido-2’,3’-dideoxythimidine is one of the most significant anti-HIV prodrug, which is currently in clinical trials. Chapters review the synthesis; physical and spectral properties (1H, 13C, 31P and 17O NMR data); characteristic reactions; important classes of compounds based on these esters of H-phosphonic acid; their application as physiologically active substances, flame retardants, catalysts, heat and light stabilizers, lubricants, scale inhibitors, polymer-carriers of drugs; preparation of H-phosphonate diesters and general procedures for conducting the most important reactions. * provides ideas for the synthesis of phosphonates, phosphoramides and diesters of phosphonic acid (new phosphorus-containing compounds)* reviews structure, spectra and biological activity of H-phosphonates and their derivatives* examines new areas of application of phosphorus-containing compounds

The Synthesis and Properties of Compounds Containing a Silicon-phosphorus Bond

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Publisher :
ISBN 13 :
Total Pages : 202 pages
Book Rating : 4.:/5 (244 download)

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Book Synopsis The Synthesis and Properties of Compounds Containing a Silicon-phosphorus Bond by : George Everett Bagley

Download or read book The Synthesis and Properties of Compounds Containing a Silicon-phosphorus Bond written by George Everett Bagley and published by . This book was released on 1959 with total page 202 pages. Available in PDF, EPUB and Kindle. Book excerpt: