Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 11
Submit an article Journal homepage
244
Views
42
CrossRef citations to date
0
Altmetric
Original Articles

Convenient Preparation of Sodium and Potassium Phenyl Selenides. Reduction of the Selenium-Selenium Bond by Sodium Hydride and Potassium Hydride

Paul Dowd Department of Chemistry, University of Pittsburgh Pittsburgh, Pennsylvania, 15260
&
Paul Kennedy Department of Chemistry, University of Pittsburgh Pittsburgh, Pennsylvania, 15260
Pages 935-941 | Published online: 05 Dec 2006

Citations (42)

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 (2)

A. Krief & M. Trabelsi. (1989) Efficient Syntheses of (d, l) and (d) Selenomethionine. Synthetic Communications 19:7-8, pages 1203-1210.
Read now
HaroldW. Pinnick. (1983) POTASSIUM HYDRIDE IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 15:3, pages 199-223.
Read now

Articles from other publishers (40)

Claudio Santi, Lucia Capoccia & Bonifacio Monti. (2018) Zinc-Selenium reagents in organic synthesis. Physical Sciences Reviews 3:12.
Crossref
Katarzyna Sidoryk, Lucie Rárová, Jana Oklešťková, Zbigniew Pakulski, Miroslav Strnad, Piotr Cmoch & Roman Luboradzki. (2016) Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins. Organic & Biomolecular Chemistry 14:43, pages 10238-10248.
Crossref
Joseph M. Zadrozny, Joshua Telser & Jeffrey R. Long. (2013) Slow magnetic relaxation in the tetrahedral cobalt(II) complexes [Co(EPh)4]2− (EO, S, Se). Polyhedron 64, pages 209-217.
Crossref
Jacek Młochowski, Rafał Lisiak & Halina Wójtowicz-Młochowska. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
Tomonori Mori, Shuhei Higashibayashi, Taiji Goto, Mitsunori Kohno, Yukiko Satouchi, Kazuyuki Shinko, Kengo Suzuki, Shunya Suzuki, Hiraku Tohmiya, Kimiko Hashimoto & Masaya Nakata. (2008) Total Synthesis of Siomycin A: Construction of Synthetic Segments. Chemistry – An Asian Journal 3:6, pages 984-1012.
Crossref
Reginaldo Bezerra dos Santos, Valdemar Lacerda Junior, Paulo Roberto Zanotto, Timothy John Brocksom & Ursula Brocksom. (2008) Regio-and Stereoselective Ring Opening of Epoxides with Sodium Phenylselenide under Phase Transfer Conditions. Journal of Chemical Research 2008:1, pages 22-25.
Crossref
Jeffrey H. Byers, Thong Nguyen & Yoshihisa Kobayashi. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Omar Boutureira, M. Isabel Matheu, Yolanda D?az & Sergio Castill?n. (2007) Synthesis of carbohydrate-based vinyl selenides via Wittig-type reactions. Carbohydrate Research 342:5, pages 736-743.
Crossref
Kazuaki Shimada, Akiko Moro-oka, Akiko Maruyama, Hiroyuki Fujisawa, Toshio Saito, Ryo Kawamura, Hisashi Kogawa, Maiko Sakuraba, Yukichi Takata, Shigenobu Aoyagi, Yuji Takikawa & Chizuko Kabuto. (2007) Synthesis of Isochalcogenazole Rings by Treating β-( N , N -Dimethylcarbamoylchalcogenenyl)alkenyl Ketones with Hydroxylamine- O -sulfonic Acid . Bulletin of the Chemical Society of Japan 80:3, pages 567-577.
Crossref
T. Wirth. 2007. Comprehensive Organometallic Chemistry III. Comprehensive Organometallic Chemistry III 457 499 .
Yaling Gong, Kazuaki Shimada, Hidenori Nakamura, Masamichi Fujiyama, Akihiro Kodama, Miyuki Otsuki, Rei Matsumoto, Shigenobu Aoyagi & Yuji Takikawa. (2006) Stannic chloride-induced unsymmetrical CSe bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes: Novel generation of selenoaldehydes. Heteroatom Chemistry 17:2, pages 125-135.
Crossref
Noboru Sonoda, Akiya Ogawa & Francesco Recupero. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Kazuaki Shimada, Seiji Oikawa, Hidenori Nakamura, Akiko Moro-oka, Miho Kikuchi, Akiko Maruyama, Takahiro Suzuki, Hisashi Kogawa, Yukiko Inoue, Yaling Gong, Shigenobu Aoyagi & Yuji Takikawa. (2005) A Preparation of Alkyl or Alkenyl N , N -Dimethylchalcogenocarbamates and Their One-Step Conversion into Symmetrical Dialkyl or Dialkenyl Dichalcogenides . Bulletin of the Chemical Society of Japan 78:5, pages 899-905.
Crossref
Kazuaki Shimada, Yaling Gong, Hidenori Nakamura, Rei Matsumoto, Shigenobu Aoyagi & Yuji Takikawa. (2005) Novel generation of selenoaldehydes through stannic chloride-induced unsymmetrical C–Se bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes. Tetrahedron Letters 46:21, pages 3775-3778.
Crossref
Dilip K. Sinha-Mahapatra, Debasis Hazra, Vedavati G. Puranik & Amitabha Sarkar. (2004) Synthesis, structure and benzannulation of chalcogen-tethered Fischer carbene complexes. Journal of Organometallic Chemistry 689:22, pages 3501-3512.
Crossref
Christopher A. Lee & Paul E. Floreancig. (2004) Studies in multidrug resistance reversal: a rapid and stereoselective synthesis of the dihydroagarofuran ring system. Tetrahedron Letters 45:39, pages 7193-7196.
Crossref
K. Rathore, K. Raghunatha Reddy, N. S. Tomer, S. M. Desai & R. P. Singh. (2004) Visible‐light‐induced controlled/living radical polymerization of styrene with a phenyl seleno group at one terminal chain end: 1‐(Phenylseleno)ethyl benzene as a photoiniferter. Journal of Applied Polymer Science 93:1, pages 348-355.
Crossref
Shuhei Higashibayashi, Mitsunori Kohno, Taiji Goto, Kengo Suzuki, Tomonori Mori, Kimiko Hashimoto & Masaya Nakata. (2004) Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid. Tetrahedron Letters 45:19, pages 3707-3712.
Crossref
Martyn Frederickson, Laurent Vuillard & Chris Abell. (2003) Novel selenium containing non-detergent sulphobetaines. Tetrahedron Letters 44:43, pages 7925-7928.
Crossref
Asit K. Chakraborti, Mrinal K. Nayak & Lalima Sharma. (2002) Diphenyl Disulfide and Sodium in NMP as an Efficient Protocol for in Situ Generation of Thiophenolate Anion:  Selective Deprotection of Aryl Alkyl Ethers and Alkyl/Aryl Esters under Nonhydrolytic Conditions , . The Journal of Organic Chemistry 67:6, pages 1776-1780.
Crossref
Jeffrey H. Byers. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Derrick L. J. Clive, Wen Yang, Aaron C. MacDonald, Zhongren Wang & Michel Cantin. (2001) Preparation of Polycyclic Systems by Sequential 5- E xo - D igonal Radical Cyclization, 1,5-Hydrogen Transfer from Silicon, and 5- E ndo - T rigonal Cyclization . The Journal of Organic Chemistry 66:6, pages 1966-1983.
Crossref
Peter A. Jacobi, Robert W. DeSimone, Indranath Ghosh, Jiasheng Guo, Sam H. Leung & Douglas Pippin. (2000) New Syntheses of the C,D-Ring Pyrromethenones of Phytochrome and Phycocyanin. The Journal of Organic Chemistry 65:25, pages 8478-8489.
Crossref
Michio Iwaoka & Shuji Tomoda. 2000. Organoselenium Chemistry. Organoselenium Chemistry 55 80 .
Andrei A. Vasil'ev, Lars Engman, J. Peter Storm & Carl-Magnus Andersson. (1999) Preparation of Unsymmetrical Diaryl Selenides via S N Ar Reactions in η 6 -Chloroarene Transition Metal Complexes . Organometallics 18:7, pages 1318-1325.
Crossref
Ludger A. Wessjohann & Udo Sinks. (1998) Benzeneselenenyl Reagents in Organic Synthesis. Journal f�r Praktische Chemie/Chemiker-Zeitung 340:3, pages 189-203.
Crossref
Alain Krief, Cathy Delmotte & Willy Dumont. (1997) Chemoselective reduction of organoselenocyanates to diselenides and selenolates. Tetrahedron 53:36, pages 12147-12158.
Crossref
Sunggak Kim, Kwang Sub Yoon & Yong Suk Kim. (1997) Kinetic studies of intramolecular additions of alkyl radicals onto imines. Tetrahedron 53:1, pages 73-80.
Crossref
Peter A Jacobi, Jiasheng Guo, Sheila I Hauck & Sam H Leung. (1996) An improved synthesis of the C,D-ring pyrromethenone of phytochrome and phytochromobilin. Tetrahedron Letters 37:34, pages 6069-6072.
Crossref
Derrick L. J. Clive & Wen Yang. (1996) Preparation of tetrahydrofuran, ?-lactone, chromanol and pyrrolidine systems by sequential 5-exo-digonal radical cyclization, 1,5-hydrogen transfer from silicon, and 5-endo-trigonal cyclization. Chem. Commun.:14, pages 1605-1606.
Crossref
Luis E. Martínez, William A. Nugent & Eric N. Jacobsen. (1996) Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal Catalysis. The Journal of Organic Chemistry 61:22, pages 7963-7966.
Crossref
W. Russell Bowman, Peter T. Stephenson, Nicholas K. Terrett & Adrian R. Young. (1995) Radical cyclisations of imines and hydrazones. Tetrahedron 51:29, pages 7959-7980.
Crossref
Derrick L. J. Clive & Maarten H. D. Postema. (1993) trans Ring-fused bicyclic structures by 6-exo-trigonal radical closure: use of the triethylborane–stannane–air system for intramolecular radical addition to aldehydes. J. Chem. Soc., Chem. Commun.:5, pages 429-430.
Crossref
Peter A. Jacobi & Robert W. DeSimone. (1992) Tetrapyrroles. V. Formal syntheses of the ring-C,D pyrromethenones of phytochrome and phycocyanin. Tetrahedron Letters 33:42, pages 6239-6242.
Crossref
Ian W.J. Still. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 403 415 .
Peter G. Jones & Carsten Thöne. (2006) Gold complexes with selenium ligands, I. Preparation and crystal structures of phenylselenolato‐gold(I) complexes. Chemische Berichte 123:10, pages 1975-1978.
Crossref
Derrick L. J. Clive, Hartford W. Manning & Taryn L. B. Boivin. (1990) Construction of trans-ring-fused compounds by radical cyclızation. J. Chem. Soc., Chem. Commun.:14, pages 972-974.
Crossref
Roger L. Snowden & Simon M. Linder. (2004) β‐Cleavage of Bis(homoallylic) Potassium Alkoxides. Synthesis of γ‐damascone. Helvetica Chimica Acta 71:7, pages 1587-1597.
Crossref
Dennis LiottaRobert MonahanIIIIII. (1986) Selenium in Organic Synthesis. Science 231:4736, pages 356-361.
Crossref
P. DOWD & P. KENNEDY. (2016) ChemInform Abstract: CONVENIENT PREPARATION OF SODIUM AND POTASSIUM PHENYL SELENIDES. REDUCTION OF THE SELENIUM‐SELENIUM BOND BY SODIUM HYDRIDE AND POTASSIUM HYDRIDE. Chemischer Informationsdienst 13:32.
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.