Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 2
Submit an article Journal homepage
98
Views
82
CrossRef citations to date
0
Altmetric
Original Articles

Photoinduced Wolff Rearrangement of α-Diazo-β-Ketophosphonates : A Novel Entry into Substituted Phosphonoacetates

P. Callant State University of Ghent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9OOO, GENT, Belgium
,
L. D'haenens State University of Ghent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9OOO, GENT, Belgium
,
E. Van. Der Eycken State University of Ghent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9OOO, GENT, Belgium
&
M. Vandewalle State University of Ghent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9OOO, GENT, Belgium
Pages 163-167 | Published online: 05 Dec 2006

Citations (82)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (6)

Seetaram Mohapatra, Chittaranjan Bhanja, Satyaban Jena, Subhendu Chakroborty & Sabita Nayak. (2013) Advances in the Bestmann–Ohira Reagent–Assisted Regioselective Synthesis of Substituted Pyrazoles, Triazoles, and Oxazoles. Synthetic Communications 43:15, pages 1993-2007.
Read now
ZsuzsaM. Jászay, Truong Son Pham, Katalin Gönczi, Imre Petneházy & László Tőke. (2010) Efficient Solid/Liquid Phase-Transfer Catalytic Diazo Transfer Synthesis. Synthetic Communications 40:11, pages 1574-1579.
Read now
Hiroki Kumamoto, Kazuhiro Haraguchi, Hiromichi Tanaka, Keisuke Kato, Takao Nitanda, Masanori Baba, Ginger E. Dutschman & Yung-Chi Cheng. (2005) Synthesis of (±)-4′-Ethynyl and 4′-Cyano Carbocyclic Analogues of Stavudine (d4T). Nucleosides, Nucleotides & Nucleic Acids 24:2, pages 73-83.
Read now
Mary E. Neubert$suffix/text()$suffix/text(), Sandra S. Keast, Julie M. Kim, Kyle J. Miller, Rachel M. Murray, Aaron G. Norton, Raj A. Shenoy, Margaret E. Walsh & Rolfe G. Petschek. (2004) The effect of replacing a benzene ring with a saturated six-membered ring on the mesomorphic properties of 4,4′-disubstituted diphenyldiacetylenes . Liquid Crystals 31:2, pages 175-184.
Read now
Jamal Nasser, Elie About-jaudet & Noel Collignon. (1990) α-FUNCTIONAL CYCLOALKYLPHOSPHONATES I. SYNTHESIS. Phosphorus, Sulfur, and Silicon and the Related Elements 54:1-4, pages 171-179.
Read now
Susumu Ohira. (1989) Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds. Synthetic Communications 19:3-4, pages 561-564.
Read now

Articles from other publishers (76)

Manoj Dhameja & Jyoti Pandey. (2018) Bestmann–Ohira Reagent: A Convenient and Promising Reagent in the Chemical World. Asian Journal of Organic Chemistry 7:8, pages 1502-1523.
Crossref
Andreas Brunner & Lukas Hintermann. (2016) A Sequential Homologation of Alkynes and Aldehydes for Chain Elongation with Optional 13 C‐Labeling . Chemistry – A European Journal 22:8, pages 2787-2792.
Crossref
Matthew G. Lloyd, Richard J. K. Taylor & William P. Unsworth. (2016) Phosphorylated cyclopropanes in the synthesis of α-alkylidene-γ-butyrolactones: total synthesis of (±)-savinin, (±)-gadain and (±)-peperomin E. Organic & Biomolecular Chemistry 14:38, pages 8971-8988.
Crossref
Matthew G. Lloyd, Mariantonietta D'Acunto, Richard J.K. Taylor & William P. Unsworth. (2015) α-Alkylidene-γ-butyrolactone synthesis via one-pot C–H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B. Tetrahedron 71:39, pages 7107-7123.
Crossref
Matthew G. LloydRichard J. K. TaylorWilliam P. Unsworth. (2014) A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones. Organic Letters 16:10, pages 2772-2775.
Crossref
Eva-Kathrin Schillinger, Michael Kümin, Angela Digennaro, Elena Mena-Osteritz, Sylvia Schmid, Helma Wennemers & Peter Bäuerle. (2013) Guiding Suprastructure Chirality of an Oligothiophene by a Single Amino Acid. Chemistry of Materials 25:22, pages 4511-4521.
Crossref
Hidayat Hussain, Ivan R. Green, Karsten Krohn & Ishtiaq Ahmed. (2013) Advances in the total synthesis of biologically important callipeltosides: a review. Natural Product Reports 30:5, pages 640.
Crossref
P. Srihari, B. Mahankali & K. Rajendraprasad. (2012) Stereoselective total synthesis of paecilomycin E. Tetrahedron Letters 53:1, pages 56-58.
Crossref
Christopher S. Chambers, Nilesh Patel & Karl Hemming. (2010) Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines. Tetrahedron Letters 51:37, pages 4859-4861.
Crossref
Tom Wennekes, Richard J. B. H. N. van den Berg, Thomas J. Boltje, Wilma E. Donker‐Koopman, Bastiaan Kuijper, Gijsbert A. van der Marel, Anneke Strijland, Carlo P. Verhagen, Johannes M. F. G. Aerts & Herman S. Overkleeft. (2010) Synthesis and Evaluation of Lipophilic Aza‐C‐glycosides as Inhibitors of Glucosylceramide Metabolism. European Journal of Organic Chemistry 2010:7, pages 1258-1283.
Crossref
Damien Habrant, Vesa Rauhala & Ari M. P. Koskinen. (2010) Conversion of carbonyl compounds to alkynes: general overview and recent developments. Chemical Society Reviews 39:6, pages 2007.
Crossref
Zvi RappoportR. S. Edmundson. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Zvi RappoportR. S. Edmundson. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Dominique Bélanger, Xia Tong, Sadia Soumaré, Yves L. Dory & Yue Zhao. (2009) Cyclic Peptide–Polymer Complexes and Their Self‐Assembly. Chemistry – A European Journal 15:17, pages 4428-4436.
Crossref
Tomasz Fekner, Xin Li, Marianne M. Lee & Michael K. Chan. (2009) A Pyrrolysine Analogue for Protein Click Chemistry. Angewandte Chemie International Edition 48:9, pages 1633-1635.
Crossref
Tomasz Fekner, Xin Li, Marianne M. Lee & Michael K. Chan. (2009) A Pyrrolysine Analogue for Protein Click Chemistry. Angewandte Chemie 121:9, pages 1661-1663.
Crossref
David A. Evans, Jason D. Burch, Essa Hu & Georg Jaeschke. (2008) Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment. Tetrahedron 64:21, pages 4671-4699.
Crossref
Po C. Chen, Vishal Patil, William Guerrant, Patience Green & Adegboyega K. Oyelere. (2008) Synthesis and structure?activity relationship of histone deacetylase (HDAC) inhibitors with triazole-linked cap group. Bioorganic & Medicinal Chemistry 16:9, pages 4839-4853.
Crossref
Vincent Gandon & Corinne Aubert. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Anja Jatsch, Alexey Kopyshev, Elena Mena-Osteritz & Peter Bäuerle. (2008) Self-Organizing Oligothiophene−Nucleoside Conjugates:  Versatile Synthesis via “Click”-Chemistry. Organic Letters 10:5, pages 961-964.
Crossref
Po C. Chen, Rebekah E. Wharton, Pratiq A. Patel & Adegboyega K. Oyelere. (2007) Direct diazo-transfer reaction on ?-lactam: Synthesis and preliminary biological activities of 6-triazolylpenicillanic acids. Bioorganic & Medicinal Chemistry 15:23, pages 7288-7300.
Crossref
Andrea Nuzzi, Alessandro Massi & Alessandro Dondoni. (2007) Model Studies Toward the Synthesis of Thymidine Oligonucleotides with Triazole Internucleosidic Linkages Via Iterative Cu(I)‐Promoted Azide–Alkyne Ligation Chemistry . QSAR & Combinatorial Science 26:11-12, pages 1191-1199.
Crossref
Steven P. Govek & Larry E. Overman. (2007) Total synthesis of (+)-asperazine. Tetrahedron 63:35, pages 8499-8513.
Crossref
Shannon D. Zanatta. (2007) The Bestmann - Ohira Reagent for the Conversion of Aldehydes into Terminal Alkynes. Australian Journal of Chemistry 60:12, pages 963.
Crossref
Konrad Kowalski, Janusz Zakrzewski, Nicholas J. Long, Sławomir Domagała & Andrew J.P. White. (2006) The synthesis and characterisation of 1′-ethynyl-2,5-dimethylazaferrocene and derivatives. Journal of Organometallic Chemistry 691:18, pages 3902-3908.
Crossref
Ernesto Quesada, Steven A. Raw, Mark Reid, Estelle Roman & Richard J.K. Taylor. (2006) One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide. Tetrahedron 62:28, pages 6673-6680.
Crossref
Russell J. Cox, Jennifer S. Gibson & Andrea T. Hadfield. (2005) Design, Synthesis and Analysis of Inhibitors of Bacterial Aspartate Semialdehyde Dehydrogenase. ChemBioChem 6:12, pages 2255-2260.
Crossref
R. Karl Dieter & Michael J. Coghlan. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Ernesto Quesada & Richard J.K. Taylor. (2005) One-pot conversion of activated alcohols into terminal alkynes using manganese dioxide in combination with the Bestmann–Ohira reagent. Tetrahedron Letters 46:38, pages 6473-6476.
Crossref
Vijay Narayanan, Sethuraman Sankararaman & Henning Hopf. (2005) Synthesis of Shape‐Persistent Polyal Dendrimers – Facile Entry to Polyene and Polyyne Dendrimers. European Journal of Organic Chemistry 2005:13, pages 2740-2746.
Crossref
Sang-Hyeup Lee, Kazuhiro Yoshida, Hana Matsushita, Bruce Clapham, Guido Koch, Jürg Zimmermann & Kim D. Janda. (2004) N−H Insertion Reactions of Primary Ureas:  The Synthesis of Highly Substituted Imidazolones and Imidazoles from Diazocarbonyls. The Journal of Organic Chemistry 69:25, pages 8829-8835.
Crossref
Alessandro Dondoni, Pier Paolo Giovannini & Alessandro Massi. (2004) Assembling Heterocycle-Tethered C -Glycosyl and α-Amino Acid Residues via 1,3-Dipolar Cycloaddition Reactions . Organic Letters 6:17, pages 2929-2932.
Crossref
Jehrod B. Brenneman, Rainer Machauer & Stephen F. Martin. (2004) Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis. Tetrahedron 60:34, pages 7301-7314.
Crossref
Edelmiro Momán, Daniel Nicoletti & Antonio Mouriño. (2004) Synthesis of Novel Analogues of 1α,25-Dihydroxyvitamin D 3 with Side Chains at C-18 . The Journal of Organic Chemistry 69:14, pages 4615-4625.
Crossref
Leonid Breydo, Hong Zang & Kent S. Gates. (2004) Synthesis and noncovalent DNA-binding properties of thiazole derivatives related to leinamycin. Tetrahedron Letters 45:29, pages 5711-5716.
Crossref
Masashi Suzuki, Mika Kambe, Hidetoshi Tokuyama & Tohru Fukuyama. (2004) Enantioselective Total Synthesis of FR900482. The Journal of Organic Chemistry 69:8, pages 2831-2843.
Crossref
Hubert Maehr & Milan R. Uskokovic. (2004) Formal Desymmetrization of the Diastereotopic Chains in Gemini Calcitriol Derivatives with Two Different Side Chains at C‐20. European Journal of Organic Chemistry 2004:8, pages 1703-1713.
Crossref
Raffaella Faraoni, Muriel Blanzat, Stefan Kubicek, Christophe Braun, W. Bernd Schweizer, Volker Gramlich & François Diederich. (2004) New Rebek imide-type receptors for adenine featuring acetylene-linked π-stacking platforms. Org. Biomol. Chem. 2:14, pages 1962-1964.
Crossref
Jos? M. Aurrecoechea, Jes?s H. Gil & Beatriz L?pez. (2003) Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides. Tetrahedron 59:36, pages 7111-7121.
Crossref
Jörg Pietruszka, Andreas Witt & Wolfgang Frey. (2003) Synthesis of “Garner” Aldehyde‐Derived Cyclopropylboronic Esters. European Journal of Organic Chemistry 2003:16, pages 3219-3229.
Crossref
Philippe Savignac & Bogdan Iorga. 2003. Modern Phosphonate Chemistry. Modern Phosphonate Chemistry.
Philippe Savignac & Bogdan Iorga. 2003. Modern Phosphonate Chemistry. Modern Phosphonate Chemistry.
William R.F Goundry, Jack E Baldwin & Victor Lee. (2003) Total synthesis of cytotoxic sponge alkaloids hachijodines F and G. Tetrahedron 59:10, pages 1719-1729.
Crossref
Arun K. Ghosh, Alexander Bischoff & John Cappiello. (2003) Asymmetric Total Synthesis of the Gastroprotective Microbial Agent AI‐77‐B. European Journal of Organic Chemistry 2003:5, pages 821-832.
Crossref
Isabelle Gillaizeau, Irene M. Lagoja, Steve P. Nolan, Vincent Aucagne, Jef Rozenski, Piet Herdewijn & Luigi A. Agrofoglio. (2003) Straightforward Synthesis of Labeled and Unlabeled Pyrimidine d4Ns via 2′,3′ ‐ Diyne seco Analogues through Olefin Metathesis Reactions . European Journal of Organic Chemistry 2003:4, pages 666-671.
Crossref
Moisés Romero-Ortega, David A. Colby & Horacio F. Olivo. (2002) Synthesis of the C10–C17 fragment of aurisides and callipeltosides. Tetrahedron Letters 43:36, pages 6439-6441.
Crossref
Hui-Ping Guan, Yao-Ling Qiu, Mohamad B. Ksebati, Earl R. Kern & Jiri Zemlicka. (2002) Synthesis of phosphonate derivatives of methylenecyclopropane nucleoside analogues by alkylation?elimination method and unusual opening of cyclopropane ring. Tetrahedron 58:30, pages 6047-6059.
Crossref
Patrick Meffre, Sébastien Hermann, Philippe Durand, Gianna Reginato & Antonella Riu. (2002) Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde. Tetrahedron 58:25, pages 5159-5162.
Crossref
Kazunobu Kira, Akinari Hamajima & Minoru Isobe. (2002) Synthesis of the BCD-ring of ciguatoxin 1B using an acetylene cobalt complex and vinylsilane strategy. Tetrahedron 58:10, pages 1875-1888.
Crossref
Marc Nazaré & Herbert Waldmann. (2001) Enantiospecific Synthesis of the (9S,18R)-Diastereomer of the Leukocyte Adhesion Inhibitor Cyclamenol A. Chemistry - A European Journal 7:15, pages 3363-3376.
Crossref
Kazunobu Kira & Minoru Isobe. (2001) Synthesis of the BCDE rings of ciguatoxin 1B via an acetylene biscobalthexacarbonyl–vinylsilane strategy. Tetrahedron Letters 42:15, pages 2821-2824.
Crossref
Vincent P. Liptak & William D. Wulff. (2000) The Preparation and Evaluation of Electron Poor Benzylidene Fischer Carbene Complexes: Studies Toward the Total Synthesis of (+)-Olivin. Tetrahedron 56:52, pages 10229-10247.
Crossref
Samir Bennabi, Kesavaram Narkunan, Laurence Rousset, Denis Bouchu†Marco A Ciufolini. (2000) Conjugate propargylation of α,β-unsaturated lactones: a solution via 1,4-addition of (Z)-2-ethoxyvinyl anion. Tetrahedron Letters 41:46, pages 8873-8876.
Crossref
K. C. Nicolaou, Jinyou Xu, Fiona Murphy, Sofia Barluenga, Olivier Baudoin, Hengxu Wei, David L. F. Gray & Takashi Ohshima. (1999) Totalsynthese von Sanglifehrin A. Angewandte Chemie 111:16, pages 2599-2604.
Crossref
Xavier Serrat, Gemma Cabarrocas, Sara Rafel, Montserrat Ventura, Anthony Linden & José M. Villalgordo. (1999) A highly efficient and straightforward stereoselective synthesis of novel chiral α-acetylenic ketones. Tetrahedron: Asymmetry 10:17, pages 3417-3430.
Crossref
Thomas J.J M?ller, Markus Ansorge & Kurt Polborn. (1999) Dialkynylated and functionalized alkynylated areneCr(CO)3-complexes?syntheses and structures of carbon rich chromium-complexed benzenes. Journal of Organometallic Chemistry 578:1-2, pages 252-259.
Crossref
Paul R. Hanson, Kevin T. Sprott & Aaron D. Wrobleski. (1999) Intramolecular cyclopropanation reactions en route to novel P-heterocycles. Tetrahedron Letters 40:8, pages 1455-1458.
Crossref
Arun K. Ghosh & John Cappiello. (1998) Stereoselective synthesis of dihydroisocoumarin moiety of microbial agent AI-77-B: a Diels-Alder based strategy. Tetrahedron Letters 39:48, pages 8803-8806.
Crossref
K.C. Nicolaou & Kazunori Koide. (1997) Synthetic studies on maduropeptin chromophore 1. Construction of the aryl ether and attempted synthesis of the [7.3.0] bicyclic system. Tetrahedron Letters 38:21, pages 3667-3670.
Crossref
Patrick Meffre, Laurence Gauzy, Eric Branquet, Philippe Durand & François Le Goffic. (1996) Synthesis of optically active β,γ-alkynylglycine derivatives. Tetrahedron 52:34, pages 11215-11238.
Crossref
A.F. Khlebnikov, M.S. Novikov & R.R. Kostikov. 1996. 93 233 .
Rong-Yu Zhang & Cong-Gui Zhao. (1996) Ring-opening reactions of some phosphoryl-substituted cyclopropanes by -NH and -SH nucleophiles. Heteroatom Chemistry 7:2, pages 155-161.
Crossref
. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 727 856 .
David C. Harrowven & Shelagh T. Dennison. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 525 554 .
Toru Minami, Masashi Kamitamari, Tomohisa Utsunomiya, Tetsuya Tanaka & Junji Ichikawa. (1993) Synthesis of Annulated γ -Lactams via Intramolecular 1,3-Dipolar Cycloadditions of Functionalized N -Allyl α -Diazo Amides . Bulletin of the Chemical Society of Japan 66:5, pages 1496-1500.
Crossref
Jacob Mathew. 1993. Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2. Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2 435 474 .
Bruce H. Lipshutz & Saumitra Sengupta. 2004. Organic Reactions. Organic Reactions 135 631 .
Paul Helquist. 1991. A Research Annual. A Research Annual 143 194 .
G. Bryon Gill. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 887 912 .
Marian Miko?ajczyk, Remigiusz Zurawi?ski & Piotr Kie?basi?ski. (1989) A new synthesis of (?)-sarkomycin from a ?-ketophosphonate. Tetrahedron Letters 30:9, pages 1143-1146.
Crossref
Bernard Corbel, Dominique Hernot, Jean-Pierre Haelters & Georges Sturtz. (1987) Synthesis of α-phosphorylated cyclopentanones by intramolecularcarbenoid cyclizations of α-diazo β-keto alkylphosphonates and phosphine oxides. Tetrahedron Letters 28:52, pages 6605-6608.
Crossref
Leo A. Paquette & Annette M. DohertyLeo A. Paquette & Annette M. Doherty. 1987. Polyquinane Chemistry. Polyquinane Chemistry 209 225 .
Gerhard Maas. 1987. Organic Synthesis, Reactions and Mechanisms. Organic Synthesis, Reactions and Mechanisms 75 253 .
Ulrich Burger & Dominique Zellweger. (2004) Über die thermische, katalytische und photochemische Stickstoff‐Eliminierung des 1‐Diazo‐3‐(1‐methylcyclopenta‐2,4‐dienyl)‐2‐propanons. Helvetica Chimica Acta 69:3, pages 676-682.
Crossref
Louis S. Hegedus. (1986) Transition metals in organic synthesis annual survey covering the year 1984. Journal of Organometallic Chemistry 298, pages 207-453.
Crossref
P. CALLANT, L. D'HAENENS, E. VAN DER EYCKEN & M. VANDEWALLE. (2016) ChemInform Abstract: PHOTOINDUCED WOLFF REARRANGEMENT OF α‐DIAZO‐β‐KETOPHOSPHONATES: A NOVEL ENTRY INTO SUBSTITUTED PHOSPHONOACETATES. Chemischer Informationsdienst 15:43.
Crossref

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

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.