Bismuth(III) Chloride (BiCl<sub>3</sub>); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water

Mohammadpoor‐Baltork, Iraj; Tangestaninejad, Shahram; Aliyan, Hamid; Mirkhani, Valiollah

doi:10.1080/00397910008086878

Cited by 56 publications

(16 citation statements)

References 26 publications

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“…Acid-catalyzed ring-opening addition reactions of water and alcohols to oxiranes, especially cycloaliphatic oxiranes, occur rapidly at moderate temperatures. 17,18 A sample of microspheres (III) was refluxed for a short time with a mixture of perchloric acid and water. Under these conditions, water undergoes addition to the epoxycyclohexane group to give the corresponding glycol in high yields.…”

Section: Acid Catalyzed Epoxide Ring-opening Addition Reactionsmentioning

confidence: 99%

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Falk

Crivello

2005

J of Applied Polymer Sci

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This article describes the synthesis and surface modification of epoxy-and hydroxy-functional polymeric microspheres. The functionalized microspheres were synthesized using aqueous and nonaqueous cationic suspension photopolymerizations using multifunctional silicon-containing epoxy monomers with iodonium salt photoinitiators. Although generally solid microspheres were obtained using these techniques, macroporous spheres could be obtained though the use of porogens. Various rapid and facile acid-and base-catalyzed ring-opening addition reactions were performed on the epoxy-functional microspheres. These reactions include the additions of mercaptans, acid chlorides, isocyanates, amines, sodium azide, water, and alcohols. Similar functionalization reactions were performed on the hydroxy-functional microspheres. The particle size and size distribution were determined using scanning electron microscopy. Fourier transform infrared spectroscopy was used to monitor the functionalization reactions.

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Section: Acid Catalyzed Epoxide Ring-opening Addition Reactionsmentioning

confidence: 99%

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Falk

Crivello

2005

J of Applied Polymer Sci

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“…[18][19][20] The Lewis acid BF 3 *Et 2 O activates the epoxide ring by accepting an electron pair of the epoxide oxygen. A complex with a positive partial charge is formed.…”

Section: Synthesis Of Graft Polymersmentioning

confidence: 99%

Grafting of Polystyrene onto Poly(butyl acrylate) and Polystyrene Backbones Using Functionalized Methacrylates

Böhme

Peppers

Schmidt‐Naake

2004

Macro Chemistry & Physics

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Summary: Grafting of terminal epoxide‐functionalized polystyrene onto poly[styrene‐co‐(2‐hydroxyethyl methacrylate)] or poly[(butyl acrylate)‐co‐(2‐hydroxyethyl methacrylate)] backbones was carried out by coupling reactions catalyzed by boron trifluoride. The functionalized backbones were prepared by free radical copolymerization of 2‐hydroxyethyl methacrylate (HEMA) with styrene or butyl acrylate. For the synthesis of terminal functionalized polymer chains a side reaction of the TEMPO‐mediated free radical polymerization of methacrylates could be used successfully to convert TEMPO‐terminated polymers into terminal epoxide‐functionalized polymers by the use of glycidyl methacrylate. The number of epoxide units attached to the backbone was directly related to the TEMPO concentration during the disproportionation reaction. Taking P(S‐co‐HEMA) as well as P(BuA‐co‐HEMA) backbones in coupling reactions with different epoxy‐functionalized polystyrenes in the presence of boron trifluoride, graft polymers with up to 7 and 37 side chains per backbone were produced.Molecular weight distribution curves of a linking experiment between P(BuA‐co‐HEMA) backbones and epoxide‐functionalized polystyrene side chains.magnified imageMolecular weight distribution curves of a linking experiment between P(BuA‐co‐HEMA) backbones and epoxide‐functionalized polystyrene side chains.

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“…[10] In connection with our ongoing work on catalysis by Bi(II) salts, [11][12][13][14] we herein report a simple and efficient method for the cleavage of tetrahydropyranyl ethers using BiCl 3 , Bi(TFA) 3 and Bi(OTf ) 3 as catalysts (Scheme 1). [10] In connection with our ongoing work on catalysis by Bi(II) salts, [11][12][13][14] we herein report a simple and efficient method for the cleavage of tetrahydropyranyl ethers using BiCl 3 , Bi(TFA) 3 and Bi(OTf ) 3 as catalysts (Scheme 1).…”

Section: Efficient Deprotection Of Tetrahydropyranyl Ethers By Bismutmentioning

confidence: 99%

Efficient Deprotection of Tetrahydropyranyl Ethers by Bismuth(iii) Salts

Mohammadpoor‐Baltork

Kharamesh

Kolagar

2002

Synthetic Communications

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Bismuth(III) Chloride (BiCl₃); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water

Cited by 56 publications

References 26 publications

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Grafting of Polystyrene onto Poly(butyl acrylate) and Polystyrene Backbones Using Functionalized Methacrylates

Efficient Deprotection of Tetrahydropyranyl Ethers by Bismuth(iii) Salts

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Bismuth(III) Chloride (BiCl3); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water

Cited by 56 publications

References 26 publications

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Synthesis and modification of epoxy‐ and hydroxy‐functional microspheres

Grafting of Polystyrene onto Poly(butyl acrylate) and Polystyrene Backbones Using Functionalized Methacrylates

Efficient Deprotection of Tetrahydropyranyl Ethers by Bismuth(iii) Salts

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Product

Resources

About

Bismuth(III) Chloride (BiCl₃); An Efficient Catalyst for Mild, Regio- and Stereoselective Cleavage of Epoxides with Alcohols, Acetic Acid and Water