Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 13
Submit an article Journal homepage
99
Views
31
CrossRef citations to date
0
Altmetric
Original Articles

An Easy Procedure for the Highly Regioselective Conversion of Epoxides to Halohydrins

Carlo Bonini Dipartimento di Chimica, Università della Basilicata, Via N.Sauro 85, 85100, Potenza
,
Claudio Giuliano Centro C.N.R. per lo Studio della Chimica delle Sostanze Organiche Naturali, c/o Dipartimento di Chimica, Università “La Sapienza” P.le A. Moro 5, 00185, Roma, Italy
,
Giuliana Righi Centro C.N.R. per lo Studio della Chimica delle Sostanze Organiche Naturali, c/o Dipartimento di Chimica, Università “La Sapienza” P.le A. Moro 5, 00185, Roma, Italy
&
Leudo Rossi Centro C.N.R. per lo Studio della Chimica delle Sostanze Organiche Naturali, c/o Dipartimento di Chimica, Università “La Sapienza” P.le A. Moro 5, 00185, Roma, Italy
Pages 1863-1870 | Accepted 24 Feb 1992, Published online: 23 Sep 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)

S. Munavalli, D.K. Rohrbaugh, R.A. Mackay, F.R. Longo & H.D. Durst. (2005) Reaction of Epoxides with (Alkylthio)methyl Chloride. Phosphorus, Sulfur, and Silicon and the Related Elements 180:12, pages 2689-2700.
Read now
Bahman Tamami, Iraj Ghazi & Hossein Mahdavi. (2002) POLYVINYLPYRROLIDONE/THIONYL CHLORIDE AS A NEW POLYMERIC REAGENT FOR FACILE CONVERSION OF EPOXIDES TO β-CHLOROHYDRINS. Synthetic Communications 32:24, pages 3725-3731.
Read now
N. Iranpoor, F. Kazemi & P. Salehi. (1997) Highly Regio- and Stereoselective Synthesis of β-Halohydrins from Epoxides Catalyzed with Ceric Ammonium Nitrate. Synthetic Communications 27:7, pages 1247-1258.
Read now

Articles from other publishers (28)

Bing Jiang, Huai-Zhu Li, Rui-Jun Li, Jianye Zhang & Yun-Xiao Zhang. (2022) Selective Oxidative Cleavage of the C–C Bond in α,β-Epoxy Ketone into Carbonyl Compounds. ACS Omega 7:25, pages 21608-21614.
Crossref
Minseok Jeon, Chaeyoung Yun & SungYong Seo. (2022) Stereoselective Synthesis of Cyclohexane Derivatives: Tandem Lithium Iodide Mediated Intramolecular Conjugate Addition of Thiols to α,β-Bisenones. Synthesis 54:12, pages 2865-2875.
Crossref
Richard C. LarockRichard C. Larock & Shilpa A. Worlikar. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 106 .
Giuliana Righi, Paolo Bovicelli, Maurizio Barontini & Ilaria Tirotta. (2012) Dimethyl carbonate in the regio- and stereocontrolled opening of three-membered heterocyclic rings. Green Chemistry 14:2, pages 495.
Crossref
Stephan D. Stamatov & Jacek Stawinski. (2007) Regioselective and stereospecific opening of an oxirane system mediated by trifluoroacetic acid and halide anions. A new direct approach to C3-vicinal halohydrins. Tetrahedron Letters 48:11, pages 1887-1889.
Crossref
André B. Charette, J. Kent Barbay & Wei He. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
James S. Nowick, Guido Lutterbach, J. Kent Barbay & Wei He. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Andr? B. Charette, J. Kent Barbay & Wei He. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
G. Smitha & Ch. Sanjeeva Reddy. (2019) Facile and regioselective conversion of epoxides into β-chlorohydrins using ZrCl 4 . Journal of Chemical Research 2004:4, pages 300-301.
Crossref
Yoshihide Tomata, Minoru Sasaki, Keiji Tanino & Masaaki Miyashita. (2003) The first C2 selective halide substitution reaction of 2,3-epoxy alcohols by the use of (CH3O)3B–MX (X=I, Br, Cl) system. Tetrahedron Letters 44:50, pages 8975-8977.
Crossref
Hashem Sharghi & Mohammad Mehdi Eskandari. (2003) Conversion of epoxides into halohydrins with elemental halogen catalyzed by thiourea. Tetrahedron 59:43, pages 8509-8514.
Crossref
Ivan Infante, Carlo Bonini, Francesco Lelj & Giuliana Righi. (2003) A First Theoretical Study on the Origin of the Metal-Mediated Regioselective Opening of 2,3-Epoxy Alcohols. The Journal of Organic Chemistry 68:10, pages 3773-3780.
Crossref
Paolo Lupattelli, Carlo Bonini, Leonilde Caruso & Augusto Gambacorta. (2003) Single Route to Chiral s yn - and a nti -2-Amino-1,2-diphenylethanols via a New Stereodivergent Opening of trans -1,2-Diphenyloxirane . The Journal of Organic Chemistry 68:8, pages 3360-3362.
Crossref
André B. Charette. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
James S. Nowick & Guido Lutterbach. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
André B. Charette. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
S Munavalli, D.K Rohrbaugh, D.I Rossman, L.R McMahon & H.D Durst. (1999) Trifluoromethylthiocopper-mediated oxirane ring opening. Journal of Organometallic Chemistry 587:2, pages 160-164.
Crossref
Giuliana Righi, Paolo Bovicelli & Anna Sperandio. (1999) A mild preparation of α-halo-α,β-enones from cyclic enones. Tetrahedron Letters 40:32, pages 5889-5892.
Crossref
Yoshiji Takemoto, Toshiro Ibuka, Hiroki Hayase, Akiko Iwanaga, Saori Yamagata, Chuzo Iwata & Tetsuaki Tanaka. (1998) Stereoselective synthesis of cis-fused chlorinated bicyclic ethers via CAN-mediated ring-opening of cyclopropyl sulfides. Tetrahedron Letters 39:41, pages 7545-7548.
Crossref
Herbert C. Brown & Chandra Deo Roy. (1998) Dibromoborane-Dimethyl Sulfide and Monobromoborane-Dimethyl Sulfide as Superior Reagents for the Opening of Oxiranes to Bromohydrins. Molecules Online 2:8, pages 114-120.
Crossref
Hashem Sharghi, Ahmad Reza Massah, Hossein Eshghi & Khodabakhsh Niknam. (1998) Crown Ethers as New Catalysts in the Highly Regioselective Halogenative Cleavage of Epoxides with Elemental Halogen. The Journal of Organic Chemistry 63:5, pages 1455-1461.
Crossref
Braja G. Hazra, Tirunahari Pavan Kumar & Padmakar L. Joshi. (2006) New Synthesis of 28‐Homobrassinolide from Stigmasterol. Liebigs Annalen 1997:5, pages 1029-1034.
Crossref
Giuliana Righi, Giovanna Rumboldt & Carlo Bonini. (1996) Stereoselective Preparation of Syn α-Hydroxy-β-amino Ester Units via Regioselective Opening of α,β-Epoxy Esters:  Enantioselective Synthesis of Taxol C-13 Side Chain and Cyclohexylnorstatine . The Journal of Organic Chemistry 61:10, pages 3557-3560.
Crossref
Giuliana Righi, Giovanna Rumboldt & Carlo Bonini. (1995) A simple route to syn α-Amino-β-Hydroxy esters by C-2 regioselective opening of a, β-Epoxy esters with metal halides. Tetrahedron 51:48, pages 13401-13408.
Crossref
Carlo Bonini, Massimo Checconi, Giuliana Righi & Leucio Rossi. (1995) Enantio and stereoselective synthesis of (5R,6S)-6-acetoxy-hexadecanolide, a mosquito oviposition attractant pheromone. Tetrahedron 51:14, pages 4111-4116.
Crossref
. 1995. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 16 53 .
Chiara Federici, Giuliana Righi, Leucio Rossi, Carlo Bonini, Lucia Chiummiento & Maria Funicello. (1994) Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols. Tetrahedron Letters 35:5, pages 797-800.
Crossref
C. BONINI, C. GIULIANO, G. RIGHI & L. ROSSI. (2010) ChemInform Abstract: An Easy Procedure for the Highly Regioselective Conversion of Epoxides to Halohydrins.. ChemInform 23:41.
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.