Advanced search
Publication Cover
Phosphorus, Sulfur, and Silicon and the Related Elements Volume 187, 2012 - Issue 12
Submit an article Journal homepage
262
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Solvent-Free Conditions as an Eco-Friendly Strategy for Synthesis of Organophosphorus Compounds

Ghasem Marandi Shahid Bakeri High Education Center of Miandoab, Urmia University, Urmia, Iran
,
Niloufar Akbarzadeh Torbati Department of Inorganic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Reza Heydari Department of Organic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Nourallah Hazeri Department of Organic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Sayyed Mostafa Habibi-Khorassani Department of Physical Organic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Malek Taher Maghsoodlou Department of Organic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Belghais Adrom Department of Organic Chemistry, Faculty of Science, The University of Sistan and Baluchestan, Zahedan, Iran
,
Brian W. Skelton Chemistry School of Biomedical, Biomolecular and Chemical Science, University of Western Australia, Perth, Western Australia, M313, Australia
&
Mohamed Makha Chemistry School of Biomedical, Biomolecular and Chemical Science, University of Western Australia, Perth, Western Australia, M313, Australia
 show all
Pages 1450-1461 | Received 25 Dec 2011, Accepted 21 Apr 2012, Published online: 10 Sep 2012
 
Sample our Physical Sciences journals, sign in here to start your FREE access for 14 days

Abstract

A series of diverse NH- and CH-acids are used for a one-pot synthesis of stable phosphorus ylides and 1,4-diionic organophosphorus compounds by trapping of the zwitterionic intermediate from the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates under solvent-free conditions. The structural geometry for one of the products was confirmed by single crystal X-ray diffraction analysis.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT

Acknowledgments

We gratefully acknowledge financial support from the Research Council of The University of Sistan and Baluchestan, Iran.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related Research Data

Synthesis And Single Crystal X-Ray Structure Of 2-(1,3,4-Oxadiazol- 2-yl)Aniline
Source: Walter de Gruyter GmbH
Dipotassium Hydrogen Phosphate Powder Catalyzed Synthesis of Alkyl 2-(2-Alkoxy-2-oxoethyl)dinaphtho[2,1-d:1,2-f][1,3]-dioxepin-2-Carboxylates from Stabilized Phosphorus Ylides in Solvent-Free Conditions
Source: Informa UK Limited
(N-Isocyanimino)triphenylphosphorane as an Efficient Reagent for the Synthesis of 1,3,4-Oxadiazoles from 3-Substituted Benzoic Acid Derivatives
Source: Informa UK Limited
An Efficient Synthesis of Stable Phosphorus Ylides Derived from Pyrazole and Indazole
Source: Informa UK Limited
Microwave-assisted solid-phase synthesis of hydantoin derivatives
Source: HAL CCSD
Passerini multicomponent reaction of indane-1,2,3-trione: an efficient route for the one-pot synthesis of sterically congested 2,2-disubstituted indane-1,3-dione derivatives
Source: FapUNIFESP (SciELO)
Study of reaction between triphenylphosphine and activated acetylenic esters in the presence of benzanilide and some its derivatives
Source: SAGE Publications
Solvent-free Wittig olefination with stabilized phosphoranes—scope and limitations
Source: Royal Society of Chemistry (RSC)
SYNTHESIS OF HIGHLY ELECTRON-POOR ALKENES FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES AND NINHYDRIN VIA INTERMOLECULAR WITTIG REACTION
Source: Informa UK Limited
A Simple Synthesis of Stable Phosphorus Ylides from Indole and Some of Its Derivatives
Source: Informa UK Limited
Dipotassium Hydrogen Phosphate Powder Catalyzed Conversion of Dialkyl 2-(2,5-Dihydroxyphenyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates to Alkyl 6-Hydroxy-2-oxo-2H-chromen-4-carboxylates
Source: Informa UK Limited
Cycloalkenes by intramolecular wittig reaction
Source: Elsevier BV
404. The adducts from triphenylphosphine and dimethyl acetylenedicarboxylate
Source: Royal Society of Chemistry (RSC)
Vicinal Proton Coupling in Nuclear Magnetic Resonance
Source: American Chemical Society (ACS)
Synthesis of Heterocyclic Pentavalent Phosphorus Compounds from Phosphite Derivatives and Indane-1,2,3-Trione
Source: Informa UK Limited
Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives
Source: ARKAT USA, Inc.
Silica Gel Catalyzed Conversion of Dialkyl 2-(1-Hydroxy-2-naphthyl)-3-(triphenylphosphoranylidene)butanedioates to Alkyl 2-Oxo-2 H -benzo[ h ]chromene-4-carboxylates in Solvent-Free Conditions
Source: Informa UK Limited
One-Pot Synthesis of Stable Phosphorus Ylides Using CH-Acid Compounds
Source: Informa UK Limited
Four-Component Synthesis of Dialkyl 2-(1,3-Dioxo-1,3-dihydro-2H-inden-2-yliden)-3-(2,2,2-trifluoroethoxy)succinates from Triphenylphosphine, Acetylenic Esters, 2,2,2-Trifluoroethanol, and Ninhydrin
Source: Informa UK Limited
Stereoselective Conversion of Stabilized Phosphorus Ylides to Dialkyl 2-(2-Nitro-phenoxy)-2-butenedioates in the Presense of Silica Gel in Solvent-Free Conditions
Source: Informa UK Limited
Dipotassium Hydrogen Phosphate Powder Catalyzed Stereoselective O-Vinylation of 1-(2-Hydroxy-1-naphthyl)-1-ethanone
Source: Informa UK Limited
A novel three-component reaction of a secondary amine and a 2-hydroxybenzaldehyde derivative with an isocyanide in the presence of silica gel: an efficient one-pot synthesis of benzo[b]furan derivatives
Source: Elsevier BV
An efficient synthesis of stable sulfur-containing phosphoranes derived from 2-mercapto-1-methylimidazole and 2-thiazoline-2-thiol
Source: Informa UK Limited
Solvent-free mechanochemical synthesis of phosphonium saltsElectronic supplementary information (ESI) available: X-ray diffraction patterns of 1. See http://www.rsc.org/suppdata/cc/b1/b111515d/
Source: Royal Society of Chemistry (RSC)
Reaktionen von vinylketonen mit stabilisierten phosphoniumyliden
Source: Elsevier BV
Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update
Source: American Chemical Society (ACS)
An efficient method for synthesis of stable phosphorus ylides and 1,4-diionic organophosphorus compounds in the presence of sodium dodecyl sulfate in aqueous media
Source: Elsevier BV
Solvent-free organic syntheses. using supported reagents and microwave irradiation
Source: Royal Society of Chemistry (RSC)
Synthesis and Reactions of Stabilized Phosphorus Ylides
Source: Bentham Science Publishers Ltd.
Three-Component Reaction of Isocyanides and 2-Formylbenzoic Acid with Dibenzylamine Catalyzed by Silica Nanoparticles under Solvent-Free Conditions
Source: Wiley
The relationship between proton-proton NMR coupling constants and substituent electronegativities—I : An empirical generalization of the karplus equation
Source: Elsevier BV
A short history of SHELX
Source: International Union of Crystallography (IUCr)
A facile synthesis of stable 1,4-diionic phosphorus compounds
Source: Elsevier BV
CCDC 760455: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
The Reaction of (N‐Isocyanimino)triphenylphosphorane with Biacetyl in the Presence of Aromatic Carboxylic Acids: Efficient One‐Pot Three‐Component Reaction for the Synthesis of 3‐(5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)‐3‐hydroxybutan‐2‐one Derivatives
Source: Wiley
Solvent-free organic syntheses. using supported reagents and microwave irradiation
Source: Royal Society of Chemistry (RSC)
Silica Gel Catalyzed Conversion of Dialkyl 2-(2-Hydroxy-1-naphthyl)-3-(1,1,1-triphenyl-λ 5 -phosphanylidene) Succinates to Alkyl 3-Oxo-3 H -benzo[ f ]chromene-1-carboxylates in Solvent-free Conditions
Source: Informa UK Limited
1,4-Diionic organophosphorus compounds
Source: Elsevier BV
Mechanically Induced Solid-State Generation of Phosphorus Ylides and the Solvent-Free Wittig Reaction
Source: American Chemical Society (ACS)
Study of reaction between activated acetylenes and N,N′-diethyl-2-thiobarbituric acid in the presence of isocyanides or triphenylphosphine
Source: Wiley
Silica Gel Catalyzed Conversion of Dimethyl 2-(5-Bromo-2-hydroxyphenyl)-3-(triphenylphosphoranylidene)butanedioate to Methyl 6-Bromo-2-oxo-2H-chromene-4-carboxylate in Solvent-Free Conditions
Source: Informa UK Limited
A Simple Synthesis of Stable Phosphorus Ylides Derived from 2-Benzoxazolinone and 2-Mercaptobenzoxazole
Source: Informa UK Limited
The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives : A novel synthesis of 2 -aryl -1,3,4 -oxadiazole derivatives
Source: Elsevier BV
Solvent-free organic syntheses. using supported reagents and microwave irradiation
Source: Royal Society of Chemistry (RSC)
Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines
Source: Elsevier BV
Three component reaction of indane-1,2,3-trione, tosylmethyl isocyanide and benzoic acid derivatives
Source: ARKAT USA, Inc.
Three‐Component Reaction of an Isocyanide and a Dialkyl Acetylenedicarboxylate with a Phenacyl Halide in the Presence of Water: An Efficient Method for the One‐Pot Synthesis of γ‐Iminolactone Derivatives
Source: Wiley
A simple synthesis of stable phosphorus ylides from reaction between triphenylphosphine and acetylenic esters in the presence of CH-acid compounds
Source: ARKAT USA, Inc.
Stereoselective Synthesis and Single Crystal X-Ray Structures of Some Sterically Congested Electron-poor N-Vinyl Pyrazole Derivatives
Source: Walter de Gruyter GmbH
Microwave Induced Conversion of Dialkyl 2-(3-Acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene)Butanedioates to Dialkyl 2-(3-Acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in the Presence of Silica Gel Powder in Solvent-Free Conditions
Source: Informa UK Limited
(N-Isocyanimino)triphenylphosphorane-Mediated, One-Pot, Efficient Synthesis of Sterically Congested 1,1,1-Trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol Derivatives via Intramolecular Aza-Wittig Reaction
Source: Informa UK Limited
A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation
Source: Elsevier BV
Stereospecific synthesis of (R)- and (S)-isophosphamide
Source: American Chemical Society (ACS)
(N-Isocyanimino)triphenylphosphorane-Catalyzed Stereoselective O-Vinylation of N-Hydroxyimides
Source: Informa UK Limited
The reaction of (N‐isocyanimino) triphenylphosphorane with an electron‐poor α‐haloketone in the presence of aromatic carboxylic acids: A novel three‐component reaction for the synthesis of disubstituted 1,3,4‐oxadiazole derivatives
Source: Wiley
One-Pot Diastereoselective Synthesis of Densely Functionalized 2H-Indeno[2,1-b]furans. Single-Crystal X-Ray Structure of Dimethyl 8,8a-Dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan-2,3-di­carboxylate
Source: (:unav)
Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, N,N-dicyclohexylcarbodiimide and (N-isocyanimino)triphenylphosphorane
Source: Springer Nature
The reaction of (N-isocyanimino)triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1,3-diphenyl-1,3-propanedione: a novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioates
Source: Elsevier BV
Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines
Source: Walter de Gruyter GmbH
A facile synthesis of diastereoisomeric 1,4-diionic organophosphorus compounds
Source: Elsevier BV
Novel one-pot, four-component condensation reaction: an efficient approach for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives by a Ugi-4CR/aza-Wittig sequence.
Source: American Chemical Society (ACS)
Microwave-Induced Conversion of Stabilized Phosphorus Ylides to Electron-Poor 2 H -Cheromenes in the Presence of Silica Gel Powder in Solvent-Free Conditions
Source: Informa UK Limited
WinGX suite for small-molecule single-crystal crystallography
Source: International Union of Crystallography (IUCr)
MICROWAVE INDUCED SYNTHESIS OF COUMARINS FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES IN THE PRESENCE OF SILICA GEL POWDER IN SOLVENT-FREE CONDITIONS
Source: Informa UK Limited
One-Pot Stereoselective Synthesis of Alkyl (Z)-2-[4-Oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates from Acetylenic Esters and N, N′ -Diphenylthiourea
Source: Informa UK Limited
The Reaction of (N-Isocyanimino)triphenylphosphorane with Anthranilic Acid Derivatives: One-Pot Synthesis of 2-Substituted 1,3,4-Oxadiazoles via Intramolecular Aza-Wittig Reaction
Source: Informa UK Limited

Linking provided by 

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.