Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 5
Submit an article Journal homepage
122
Views
31
CrossRef citations to date
0
Altmetric
Original Articles

A Convenient Propargylating Agent. 3-Bromo-1-Trimethylisilyl-1-Propyne

R. Bryan Miller Department of Chemistry, University of California, Davis, California, 95616
Pages 267-272 | Received 12 Jun 1972, Published online: 05 Dec 2006

Citations (31)

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 (3)

J.P. Haelters & B. Corbel et G. Sturtz. (1989) CHLORO-1 ET CHLORO-3 METHOXYCARBONYLHYDRAZONO-2 PROPYLPHOSPHONATES: REACTIFS D'ALKYLATION D'ENOLATES DE CETONES. ACCES A DES PHOSPHONATES PYRROLIQUES ET A DES β,ε DICETOPHOSPHONATES PRECURSEURS DE CYCLOPENTENONES. Phosphorus, Sulfur, and Silicon and the Related Elements 44:1-2, pages 53-74.
Read now
A.J. Poss & M.S. Smyth. (1987) Diethyl 3-Bromopropene Phosphonate an Alkylative 8-Keto Phosphonate Equivalent. Synthetic Communications 17:14, pages 1735-1740.
Read now
R. Bryan Miller & Thomas Reichenbach. (1976) Grignard Addition to Alkynols. Synthetic Communications 6:5, pages 319-323.
Read now

Articles from other publishers (28)

Prabuddha Bhattacharya & Amit Basak. (2013) An unexpected one step domino conversion of TMS-alkynes to protected ketones in 4-chromenone system. Tetrahedron Letters 54:37, pages 5137-5139.
Crossref
Adriano Carpita, Luca Mannocci & Renzo Rossi. (2005) Silver(I)-Catalysed Protiodesilylation of 1-(Trimethylsilyl)-1-alkynes. European Journal of Organic Chemistry 2005:9, pages 1859-1864.
Crossref
Carol K. Wada. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Amos B. Smith III, David A. Favor, Paul A. Sprengeler, Mark C. Guzman, Patrick J. Carroll, George T. Furst & Ralph Hirschmann. (1999) Molecular modeling, synthesis, and structures of N-methylated 3,5-linked pyrrolin-4-ones toward the creation of a privileged nonpeptide scaffold. Bioorganic & Medicinal Chemistry 7:1, pages 9-22.
Crossref
Gary A. Molander & Carlos del Pozo Losada. (1998) Sequential epoxide fragmentation/radical cyclizations mediated by samarium(II) iodide. Tetrahedron 54:22, pages 5819-5832.
Crossref
Yufu Owada, Takeshi Matsuo & Nobuharu Iwasawa. (1997) Transformation of 1-(1,2-propadienyl)cyclopropanols into substituted hydroquinones employing octacarbonyldicobalt. Tetrahedron 53:32, pages 11069-11086.
Crossref
Edwin C Davison, Ian T Forbes, Andrew B Holmes & Jacqueline A Warner. (1996) N-Alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 8. The scope of tandem reactions involving hydroxylamine-alkyne cyclisations. Tetrahedron 52:35, pages 11601-11624.
Crossref
Carole Schmitz, Anne-Claire Rouanet-Dreyfuss, Marie Tueni & Jean-François Biellmann. (1996) Syntheses of (−)-Isocitric Acid Lactone and (−)-Homoisocitric Acid. A New Method of Conversion of Alkynylsilanes into the Alkynyl Thioether and Corresponding Carboxylic Acids. The Journal of Organic Chemistry 61:5, pages 1817-1821.
Crossref
Jack E. Baldwin, Sean C. MacKenzie Turner & Mark G. Moloney. (1994) The synthesis of substituted pyrrolidines by a samarium (II) iodide mediated ring closure. Part 2. Tetrahedron 50:31, pages 9425-9438.
Crossref
Carole Schmitz, Anne-Claire Rouanet-Dreyfuss, Marie Tueni & Jean-François Biellman. (1992) Short and efficient syntheses of (−) -isocitric acid lactone and (−) -homoisocitric acid. Conversion of alkynylsilanes into the corresponding carboxylic acids. Tetrahedron Letters 33:34, pages 4911-4912.
Crossref
Bernard Mauzé & Léone Miginiac. (1991) Synthèse régiosélective de silanes α-fonctionnels par alkylation du dérivé lithié du triméthylsilylacétonitrile. Journal of Organometallic Chemistry 411:1-2, pages 69-74.
Crossref
Danielle Mesnard & Léone Miginiac. (1991) Allénylsilanes fonctionnels: synthése régiosélective par voie organoaluminique d'alcools alléniques triméthylsilylés α′ - ou ω′-chlorés. Journal of Organometallic Chemistry 403:3, pages 299-309.
Crossref
D. Mesnard & L. Miginiac. (1990) Alcynylsilanes fonctionnels I. Synthèse régiospécifique par voie organozincique d'alcools homopropargyliques trialkylsilylés α′ - ou ω′-chlorés. Journal of Organometallic Chemistry 397:2, pages 127-137.
Crossref
David J. W. Goon, James A. Elberling, E. G. Demaster & Herbert T. Nagasawa. (2006) Synthesis of [ 14 C]‐pargyline {N‐methyl‐N‐([1‐ 14 C]‐propargyl)benzylamine} with the radioactive label on the propargyl group . Journal of Labelled Compounds and Radiopharmaceuticals 28:2, pages 203-208.
Crossref
Cheryl D. Buttery, Andrew G. Cameron, Colin P. Dell & David W. Knight. (1990) A total synthesis of the guaiane furanosesquiterpene (±)-gnididione, a metabolite of Gnidia latifolia. J. Chem. Soc., Perkin Trans. 1:6, pages 1601-1610.
Crossref
Paul A. Wender & Frank E. McDonald. (1990) Studies on tumor promoters. 10. Synthesis of the abc ring system of the tiglianes and daphnanes by a zirconium-mediated intramolecular enyne carbocyclization. Tetrahedron Letters 31:26, pages 3691-3694.
Crossref
G. Courtois & L. Miginiac. (1989) Etude de la régiosélectivité de l'action des organozinciques sur les α-iminoesters: synthèse d'α-aminoesters C-substitués par un groupe α-insaturé ou α-fonctionnel. Journal of Organometallic Chemistry 376:2-3, pages 235-243.
Crossref
J.F. Chollet, B. Mauze & L. Miginiac. (1989) Synthèse régioselective par voie organométallique de nouveaux aryl-1 triazolyl-2 éthanols-1 à substituants α-insaturés, composés fongicides potentiels. Journal of Organometallic Chemistry 368:1, pages 1-18.
Crossref
Henk Hiemstra, Wim J. Klaver & W. Nico Speckamp. (2010) A novel synthetic route to 6‐azabicyclo[3.2.1]oct‐3‐enes via silicon directed N ‐Acyliminium chemistry: Synthesis of (±)‐gabaculine . Recueil des Travaux Chimiques des Pays-Bas 105:9, pages 299-306.
Crossref
R.Bryan Miller & Mohammed I. Al-Hassan. (1983) The tetrahydropyranyl ether of (E)-3-bromo-3-trimethylsilyl-2-propen-1-ol, a single synthon for the (E)-β-formylvinyl anion and cation. Tetrahedron Letters 24:20, pages 2055-2058.
Crossref
Teruaki Mukaiyama & Taira Harada. (1981) A CONVENIENT SYNTHESIS OF α-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE. Chemistry Letters 10:5, pages 621-624.
Crossref
Hans‐Josef Altenbach. (2003) (Bromoacetylmethylene)triphenylphosphorane— A Novel Cyclopentannelating Agent. Angewandte Chemie International Edition in English 18:12, pages 940-941.
Crossref
Hans‐Josef Altenbach. (2006) (Bromacetylmethylen)triphenylphosphoran – ein neues Cyclopentanellierungsagens. Angewandte Chemie 91:12, pages 1005-1006.
Crossref
Edward Piers, Brian Abeysekera & John R. Scheffer. (1979) Preparation of, and alkylation of enolate anions with, dimethyl 3-bromo-2 ethoxypropenylphosphonate. An efficient, convergent synthesis of 2-cyclo-penten-1-ones. Tetrahedron Letters 20:35, pages 3279-3282.
Crossref
Karl Eiter, Folker Lieb, Hans Disselnkötter & Hermann Oediger. (2006) Synthese hochungesättigter Fettsäuren und einiger Derivate; neue C—C‐Verknüpfungsmethode zum Aufbau von Vorstufen der biologischen Prostaglandin‐Synthese. Justus Liebigs Annalen der Chemie 1978:4, pages 658-674.
Crossref
S.J. Harris & D.R.M. Walton. (1978) Silylation as a protective method in acetylene chemistry.. Tetrahedron 34:7, pages 1037-1042.
Crossref
R. B. MILLER. (2016) ChemInform Abstract: EIN EINFACHES PROPARGYLIERUNGSMITTEL, 3‐BROM‐1‐TRIMETHYLSILYL‐1‐PROPIN. Chemischer Informationsdienst 4:3.
Crossref
Herbert T. Nagasawa & Dwight S. Fullerton. 1973. 303 312 .

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.