Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 3
227
Views
63
CrossRef citations to date
0
Altmetric
Original Articles

Reaction of β-Diketones with Triphenylphosphine Dihalides: A New, Efficient Synthesis of Cyclic β-Chloro-, β-Bromo- and β-Iodo-α,β-Unsaturated Ketones

&
Pages 193-199 | Received 09 Jan 1975, Published online: 05 Dec 2006

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

Read on this site (1)

J. P. Barnier & L. Blanco. (2003) Chemo-enzymatic Preparations of (R)- and (S)-3-Iodocyclohex-2-en-1-yl Acetate. Synthetic Communications 33:14, pages 2487-2496.
Read now

Articles from other publishers (62)

François Munyemana & Léon Ghosez. (2023) A Mild Method for the Replacement of a Hydroxyl Group by Halogen: 4. Practical Synthesis of Cyclic β-Halovinylketones under Neutral Conditions. Synthesis 55:13, pages 2083-2090.
Crossref
Richard C. LarockRichard C. Larock & Li Zhang. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 62 .
Richard C. LarockRichard C. Larock & Li Zhang. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 19 .
Roland Fitzner, Elena Mena‐Osteritz, Karsten Walzer, Martin Pfeiffer & Peter Bäuerle. (2015) A–D–A‐Type Oligothiophenes for Small Molecule Organic Solar Cells: Extending the π‐System by Introduction of Ring‐Locked Double Bonds. Advanced Functional Materials 25:12, pages 1845-1856.
Crossref
Juhienah Khalaf, Maria E. Estrella-Jimenez, Matthew J. Shashack, Sharangdhar S. Phatak, Shuxing Zhang & Scott R. Gilbertson. (2011) Design, Synthesis, and Diversification of 3,5-Substituted Enone Library. ACS Combinatorial Science 13:4, pages 351-356.
Crossref
Jean-Robert Dormoy, Bertrand Castro & Matthew L. Crawley. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Maria Estrella Jimenez, Kathryn Bush, Jennifer Pawlik, Laurie Sower, Johnny W. Peterson & Scott R. Gilbertson. (2008) Synthesis and screening of small molecule inhibitors of anthrax edema factor. Bioorganic & Medicinal Chemistry Letters 18:14, pages 4215-4218.
Crossref
Nadège Boudet, Shohei Sase, Pradipta Sinha, Ching-Yuan Liu, Arkady Krasovskiy & Paul Knochel. (2007) Directed Ortho Insertion (DoI):  A New Approach to Functionalized Aryl and Heteroaryl Zinc Reagents. Journal of the American Chemical Society 129:41, pages 12358-12359.
Crossref
Louis F. Fieser, Mary Fieser & Tse-Lok HoTse-Lok Ho, Mary Fieser & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Tricia L. Scott, Xiaomei Yu, Sobha P. Gorugantula, Grissell Carrero-Martínez & Björn C.G. Söderberg. (2006) Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids. Tetrahedron 62:47, pages 10835-10842.
Crossref
Hongjun Ren & Paul Knochel. (2006) Regioselective functionalization of trisubstituted pyridines using a bromine–magnesium exchange. Chem. Commun.:7, pages 726-728.
Crossref
Ioannis Sapountzis, Henry Dube, Robert Lewis, Nina Gommermann & Paul Knochel. (2005) Synthesis of Functionalized Nitroarylmagnesium Halides via an Iodine−Magnesium Exchange. The Journal of Organic Chemistry 70:7, pages 2445-2454.
Crossref
Katsuhide Kamei, Noriko Maeda & Toshio Tatsuoka. (2005) A practical synthetic method for vinyl chlorides and vinyl bromides from ketones via the corresponding vinyl phosphate intermediates. Tetrahedron Letters 46:2, pages 229-232.
Crossref
Paul Knochel, M. Isabel Calaza & Eike Hupe. 2004. Metal‐Catalyzed Cross‐Coupling Reactions. Metal‐Catalyzed Cross‐Coupling Reactions 619 670 .
C.M Marson, L.D Farrand, R Brettle & D.A Dunmur. (2003) Highly efficient syntheses of 3-aryl-2-cycloalken-1-ones and an evaluation of their liquid crystalline properties. Tetrahedron 59:24, pages 4377-4381.
Crossref
Xiaoyong Fu, Shuyi Zhang, Jianguo Yin, Timothy L. McAllister, S.Anna Jiang, Chou-Hong Tann, T.K. Thiruvengadam & Fucheng Zhang. (2002) First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction. Tetrahedron Letters 43:4, pages 573-576.
Crossref
Jean-Robert Dormoy & Bertrand Castro. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Rafael Chinchilla & Carmen Nájera. (2000) Acylvinyl and Vinylogous Synthons. Chemical Reviews 100:6, pages 1891-1928.
Crossref
Matthias Beller & Carsten BolmPaul Knochel. 1998. Transition Metals for Organic Synthesis. Transition Metals for Organic Synthesis 467 503 .
Paul Knochel, Juan J. Almena Perea & Philip Jones. (1998) Organozinc mediated reactions. Tetrahedron 54:29, pages 8275-8319.
Crossref
Paul Knochel. 1998. Metal‐Catalyzed Cross‐Coupling Reactions. Metal‐Catalyzed Cross‐Coupling Reactions 386 419 .
A.S Bhanu Prasad & Paul Knochel. (1997) Preparation and reactions of 2-zincated 2-cyclohexen-1-one and related heterocycles. Tetrahedron 53:49, pages 16711-16720.
Crossref
A.S Bhanu Prasad, Thomas M Stevenson, Janakiram Rao Citineni, Valérie Nyzam & Paul Knochel. (1997) Preparation and reactions of new zincated nitrogen-containing heterocycles. Tetrahedron 53:21, pages 7237-7254.
Crossref
Falk Langer, Kurt Püntener, Rainer Stürmer & Paul Knochel. (1997) Preparation of polyfunctional phosphines using zinc organometallics. Tetrahedron: Asymmetry 8:5, pages 715-738.
Crossref
Falk Langer, Lothar Schwink, Arokiasamy Devasagayaraj, Pierre-Yves Chavant & Paul Knochel. (1996) Preparation of Functionalized Dialkylzincs via a Boron−Zinc Exchange. Reactivity and Catalytic Asymmetric Addition to Aldehydes. The Journal of Organic Chemistry 61:23, pages 8229-8243.
Crossref
Heinz Stadtmüller, Andrea Vaupel, Charles E. Tucker, Thomas Stüdemann & Paul Knochel. (2006) Stereoselective Preparation of Polyfunctional Cyclopentane Derivatives by Radical Nickel‐ or Palladium‐Catalyzed Carbozincations. Chemistry – A European Journal 2:10, pages 1204-1220.
Crossref
Joseph B. Lambert & Xiaoyang Liu. (1996) The β-effect of silicon in the orthogonal geometry. Journal of Organometallic Chemistry 521:1-2, pages 203-210.
Crossref
Ingo Klement, Mario Rottländer, Charles E. Tucker, Tahir N. Majid, Paul Knochel, Patricia Venegas & Gérard Cahiez. (1996) Preparation of polyfunctional aryl and alkenyl zinc halides from functionalized unsaturated organolithiums and their reactivity in cross-coupling and conjugated addition reactions. Tetrahedron 52:21, pages 7201-7220.
Crossref
. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 727 856 .
Frank S. GuziecJr.Jr. & Lynn J. Guziec. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 381 401 .
Joseph B. Sweeney. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 37 112 .
Warren J. Ebenezer & Paul Wight. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 205 276 .
Rajagopal Duddu, Matthias Eckhardt, Michael Furlong, H.Peter Knoess, Stefan Berger & Paul Knochel. (1994) Preparation and reactivity of chiral β-amido-alkylzinc iodides and related configurationally stable zinc organometallics. Tetrahedron 50:8, pages 2415-2432.
Crossref
Heinz Stadtmüller, Charles E. Tucker, Andrea Vaupel & Paul Knochel. (1993) Stereoselective synthesis of polyfunctional di- and trisubstituted cyclopentane derivatives using a new palladium catalyzed cyclization.. Tetrahedron Letters 34:49, pages 7911-7914.
Crossref
Falk Langer, Jack Waas & Paul Knochel. (1993) Preparation and reaction of new dialkylzincs obtained by a boron-zinc transmetalation.. Tetrahedron Letters 34:33, pages 5261-5264.
Crossref
Koo Lee & David F. Wiemer. (1993) The reaction of vinyl phosphates with iodotrimethylsilane: Synthesis of vinyl iodides from ketones. Tetrahedron Letters 34:15, pages 2433-2436.
Crossref
Walter Brieden, Roswitha Ostwald & Paul Knochel. (2003) Enantioselective Catalytic Addition of Functionalized Dialkylzinc Compounds to β‐Stannylated Aldehydes: A Convenient Preparation of Chiral β‐ and γ‐Functionalized Secondary Alcohols. Angewandte Chemie International Edition in English 32:4, pages 582-584.
Crossref
Walter Brieden, Roswitha Ostwald & Paul Knochel. (1993) Enantioselektive katalytische Addition funktionalisierter Dialkylzinkverbindungen an β-stannylierte Aldehyde; eine einfache Methode zur Herstellung nichtracemischer β- und γ-funktionalisierter sekundärer Alkohole. Angewandte Chemie 105:4, pages 629-631.
Crossref
Paul Knochel & C. Janakiram Rao. (1993) Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics. Tetrahedron 49:1, pages 29-48.
Crossref
S. Achyutha Rao, Tso-Sheng Chou, Ioana Schipor & Paul Knochel. (1992) Preparation and Reactivity of Polyfunctional Zinc and Copper Organometallics Bearing Sulfur Functionalities. Tetrahedron 48:11, pages 2025-2043.
Crossref
Tatsuo Ishiyama, Norio Miyaura & Akira Suzuki. (1991) Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of 1-Halo-1-alkenes with 9-Alkyl-9-BBN Derivatives. A Direct Synthesis of α,β-Unsaturated Ketones. Bulletin of the Chemical Society of Japan 64:6, pages 1999-2001.
Crossref
Hans Fischer, Michael Klippe, Holger Lerche, Theodor Severin & Gabriele Wanninger. (2006) Elektrophile β‐Bromierung und nucleophile α‐Methoxylierung α,β‐ungesättigter Carbonylverbindungen. Chemische Berichte 123:2, pages 399-404.
Crossref
Sidduri AchyuthaRao, Charles E. Tucker & Paul Knochel. (1990) Preparation of functionalized zinc and copper organometallics containing sulfur functionalities at the alpha or gamma position. Tetrahedron Letters 31:52, pages 7575-7578.
Crossref
Tahir N Majid, Ming Chang P Yeh & Paul Knochel. (1989) Synthesis and reactivity of open-chain and cyclic 2-cyano zinc and copper organometallics. Tetrahedron Letters 30:38, pages 5069-5072.
Crossref
Huai Gu Chen, Craig Hoechstetter & Paul Knochel. (1989) Mixed copper, zinc 2-amino benzylic organometallics as efficient reagents for the synthesis of heterocycles. Tetrahedron Letters 30:36, pages 4795-4798.
Crossref
Ming Chang P. Yeh, Paul Knochel, William M. Butler & Scott C. Berk. (1988) 1,4-Additions of the highly functionalized copper reagents RCu(CN)ZnI · 2 BFP3 to trisubstituted enones. A new BF3 promoted cyclization reaction. Tetrahedron Letters 29:51, pages 6693-6696.
Crossref
Toshio Sugita, Hiroshi Ito, Akihiko Nakajima, Motoshi Sunami, Atsushi Kawakatsu, Masakazu Suama & Katsuhiko Ichikawa. (1987) Chlorination of Acyclic β-Diketones. Formation and Stability of β-Chloro-β,γ-unsaturated Ketones. Bulletin of the Chemical Society of Japan 60:2, pages 721-725.
Crossref
P. Hodge & E. Khoshdel. (1985) Wittig syntheses of dihalo-olefins by reaction of carbonyl compounds with polymer-supported phosphines and carbon tetrahalides. Reactive Polymers, Ion Exchangers, Sorbents 3:2, pages 143-150.
Crossref
Jean-Claud Gramain, Henri-Philippe Husson & Yves Troin. (1985) Synthese stereospecifique par voie photochimique de trans hexahydro-1,2,3,4,4a,9a carbazolones-4 substituees en 4a1. Tetrahedron Letters 26:19, pages 2323-2326.
Crossref
Bertrand R. Castro. 2004. Organic Reactions. Organic Reactions 1 162 .
Chuan Shih & John S. Swenton. (1981) An efficient and simple β-acylvinyl anion equivalent for cyclohexenones. Tetrahedron Letters 22:42, pages 4217-4220.
Crossref
Wenling Kao & Richard W. Rees. (1978) Synthesis of (±)-16-thioketal and 16-keto prostaglandins. Prostaglandins 16:3, pages 461-465.
Crossref
Nobuhisa Okukado, David E. Van Horn, William L. Klima & Ei-ichi Negishi. (1978) A highly stereo- , regio- , and chemoselective synthesis of conjugated dienes by the palladium-catalyzed reaction of ()-1-alkenylzirconium derivatives with alkenyl halides. Tetrahedron Letters 19:12, pages 1027-1030.
Crossref
K. Mori, S. Tamada, M. Uchida, N. Mizumachi, Y. Tachibana & M. Matsui. (1978) Synthesis of optically active forms of seudenol, the pheromone of douglas fir beetle. Tetrahedron 34:13, pages 1901-1905.
Crossref
. 1978. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 336 495 .
Paul A. Wender & Stephen L. Eck. (1977) Organobiscuprates. A single-step spiroannelation method. Tetrahedron Letters 18:14, pages 1245-1248.
Crossref
P.C. Traas, H.J. Takken & H. Boelens. (1977) Versatile synthesis of α,β-unsaturated aldehydes and nitriles from ketones via vilsmeier formylation.. Tetrahedron Letters 18:23, pages 2027-2030.
Crossref
Edward Piers & Isao Nagakura. (1976) Efficient preparation and thermal rearrangement of β-(2-vinylcyclopropyl)-α,β-unsaturated ketones. Convenient cycloheptane annelations.. Tetrahedron Letters 17:37, pages 3237-3240.
Crossref
Edward Piers, Cheuk Kun Lau & Isao Nagakura. (1976) Preparation and thermal rearrangement of β-cyclopropyl-α,β-unsaturated ketones. Convenient cyclopentane annelations.. Tetrahedron Letters 17:37, pages 3233-3236.
Crossref
D.L. Venton & Matthias C. Lu. 1976. Annual Reports in Medicinal Chemistry Volume 11. Annual Reports in Medicinal Chemistry Volume 11 261 270 .
E. PIERS & I. NAGAKURA. (2016) ChemInform Abstract: REACTION OF BETA‐DIKETONES WITH TRIPHENYLPHOSPHINE DIHALIDES, A NEW, EFFICIENT SYNTHESIS OF CYCLIC BETA‐CHLORO‐, BETA‐BROMO‐ AND BETA‐IODO‐ALPHA,BETA‐UNSATURATED KETONES. Chemischer Informationsdienst 6:38.
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:

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:

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.