Special Issue "Organophosphorus Chemistry"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 July 2013)

Special Issue Editor

Guest Editor
Prof. Dr. György Keglevich
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary
Website: http://www.scirp.org/Journal/DetailedInforOfEditorialBoard.aspx?personID=3993
E-Mail: gkeglevich@mail.bme.hu
Interests: organophosphorus chemistry (P-heterocycles, phospha -Michael reactions, Kabachnik-Fields (phospha-Mannich) reaction, C-P coupling reactions); green chemistry; MW chemistry; platinum complexes with P-ligands; synthesis of dronates; phase transfer catalysis

Special Issue Information

Dear Colleagues,

These days, organophosphorus (OP) chemistry became an integrant part of synthetic organic chemistry. OP compounds are used as starting materials, reagents, catalysts (phase transfer catalysts or P(III)-transition metal complexes) and solvents (ionic liquids (IL)) in research laboratories and in the industry. A part of these applications are in the focus today. There are a lot of frequently used reactions, such as reductions, the Wittig reaction and its variations, the Arbuzov reaction, the Mitsunobu reaction etc. that apply P-containing reagents. Other reactions eg. homogeneous catalytic transformations or C-C coupling reactions involve P-ligands in the catalysts. There has been an enormous development in the field of chiral OP compounds. Methods have been elaborated for the resolution of tertiary phosphine oxides and for stereoselective OP transformations. The optically active P(III) species may be used in transition metal (Pt, Pd, etc.) complex catalysts promoting enantioselective transformations. The heterocyclic discipline may include P-heterocycles and classical O- and N-heterocycles with P-functions. A special field comprises P-containing macrocycles and other macromolecules, like dendrimers. An up-to-date approach is to perform syntheses in the OP discipline in an environmentally-friendly manner. This may include the use of microwave. At the other end, OP species (eg. catalysts and ILs) may be tools in general synthetic organic chemistry. Monitoring the reactions in order to optimize the conditions or to observe reactive species is a challenging field. Theoretical calculations within OP chemistry is also developing field; these days stereostructures and mechanisms may be easily evaluated. A very importanft segment od OP chemistry, better to say a driving force for the development, is the pool of biologically active OP compounds that are searched and used as drugs, or plant protecting agents. The natural analogue P-compounds (eg. peptide and aminoacid analogues) should also be mentioned. Lots of new phosphine oxides, phosphinates, phosphonates and phosphoric esters have been described that may obtain application on a broad scale.
The OP special issue of Molecules will welcome all kind of submissions that fit the above outline.

Prof. Dr. György Keglevich
Guest Editor

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

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Keywords

  • organophosphorus chemistry
  • phosphine chalcogenides
  • phosphines
  • phosphinic acids
  • phosphonic acids
  • phosphine boranes
  • phosphine complexes
  • P-heterocycles
  • macrocycles
  • dendrimers
  • catalysts
  • homogeneous catalysis
  • ionic liquids
  • microwave
  • monitoration
  • theoretical calculations
  • biologically active substrates

Published Papers (7 papers)

Molecules 2013, 18(11), 14268-14284; doi:10.3390/molecules181114268
Received: 8 October 2013; in revised form: 8 November 2013 / Accepted: 8 November 2013 / Published: 18 November 2013
Show/Hide Abstract | Download PDF Full-text (680 KB)

Molecules 2013, 18(10), 12845-12856; doi:10.3390/molecules181012845
Received: 1 August 2013; in revised form: 9 October 2013 / Accepted: 10 October 2013 / Published: 16 October 2013
Show/Hide Abstract | Download PDF Full-text (195 KB)
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Molecules 2013, 18(7), 8473-8484; doi:10.3390/molecules18078473
Received: 9 June 2013; in revised form: 9 July 2013 / Accepted: 15 July 2013 / Published: 18 July 2013
Show/Hide Abstract | Download PDF Full-text (550 KB)

Molecules 2012, 17(12), 14573-14587; doi:10.3390/molecules171214573
Received: 23 November 2012; in revised form: 29 November 2012 / Accepted: 5 December 2012 / Published: 7 December 2012
Show/Hide Abstract | Download PDF Full-text (263 KB)
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Molecules 2012, 17(11), 13605-13621; doi:10.3390/molecules171113605
Received: 31 October 2012; in revised form: 9 November 2012 / Accepted: 12 November 2012 / Published: 16 November 2012
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Molecules 2012, 17(11), 13530-13568; doi:10.3390/molecules171113530
Received: 17 October 2012; in revised form: 9 November 2012 / Accepted: 12 November 2012 / Published: 15 November 2012
Show/Hide Abstract | Download PDF Full-text (904 KB)

Molecules 2012, 17(11), 12821-12835; doi:10.3390/molecules171112821
Received: 18 October 2012; in revised form: 25 October 2012 / Accepted: 26 October 2012 / Published: 1 November 2012
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Type of Paper: Review
Title: Stoichiometric and Catalytic Synthesis of Alkynylphosphines
Authors: Carole Alayrac, Elise Bernoud and Annie-Claude Gaumont
Affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, ENSICAEN & Université de Caen, F-14050 Caen, France
Abstract: Alkynylphosphines are very attractive compounds due to the presence of two important functions, a phosphorus atom – a key-atom in metal coordination – and an alkynyl function, which is known to display a rich and diverse chemistry. For example their easy transformation into valuable functionalized alkenyl mono- or diphosphines  through addition reactions on the triple bond was recently demonstrated.  Despite the obvious potential of alkynylphosphines as ligands for homogeneous catalysis, only a few catalytic applications have been disclosed so far.  Importantly P-stereogenic alkynylphosphines were shown to be highly efficient ligands for the asymmetric induction of several transition-metal catalyzed reactions.  The application of alkynylphosphines as building blocks for the synthesis of new phosphines was the topic of a recent review.  Regarding the procedures for their preparation, they have been only shortly surveyed as part of a broader topic covering all 1-phosphorus-functionalized alk-1-ynes in a review published in 2006. We propose to write a comprehensive survey of the various synthetic methods either stoichiometric or catalytic towards alkynylphosphines.

Type of Paper: Review
Title: The Kabachnik–Fields Reaction; Mechanism and Synthetic Use 
Author: György Keglevich
Affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary 
Abstract: The Kabachnik–Fields (phospha-Mannich) reaction including the condensation of primary or
secondary amines, oxo compounds (aldehydes and ketones) and > P(O)H species, especially dialkyl phosphites represents a good choice for the synthesis of -aminophosphonates that are of importance due to their biological activity. In general, the three-component reaction may take place via an imine or an -hydroxyphosphonate intermediate. Monitoration of a few Kabachnik–Fields reactions by in situ Fourier transform IR spectroscopy pointed out the involvement of the imine intermediate that was also justified by theoretical calculations. The Kabachnik–Fields reaction was extended to > P(O)H species, comprising cyclic phosphites, acyclic and cyclic H-phosphinates, as well as secondary phosphine oxides. On the other hand, heterocyclic amines were also used to prepare new -amino phosphonic, phosphinic and phosphine oxide derivatives. In most cases, the synthesis under solvent-frees microwave (MW) conditions is the method of choice. It was proved that, in the cases studied by us, there was no need for the use of any catalyst. Moreover, it can be said that the sophisticated and environmentally unfriendly catalysts suggested are completely unnecessary under MW conditions. Finally, the double Kabachnik–Fields reaction made available bis(phosphonomethyl)amines, bis(phosphinoxidomethyl)amines and related species. The bis(phosphinoxidomethyl)amines served as precursors for bisphosphines that furnished ring platinum complexes on reaction with dichlorodibenzonitrileplatinum.

Last update: 5 February 2013

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