Cyclic ether synthesis from diols using trimethyl phosphate

2017 ◽  
Vol 53 (35) ◽  
pp. 4787-4790 ◽  
Author(s):  
Shota Asai ◽  
Maho Kato ◽  
Yasunari Monguchi ◽  
Hironao Sajiki ◽  
Yoshinari Sawama
Keyword(s):  
Room Temperature ◽  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Trimethyl Phosphate ◽  
Ether Synthesis

Cyclic ethers are simply synthesized from diols by using trimethyl phosphate at room temperature.

Cyclic ether synthesis: sulfenyletherification with benzenesulfenyl chloride/N, N-diisopropylethylamine and sulfenate ester cycloadditions

1987 ◽  
Vol 65 (8) ◽  
pp. 1833-1837 ◽  
Author(s):  
Sudersan M. Tuladhar ◽  
Alex G. Fallis
Keyword(s):  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Nucleophilic Displacement ◽  
Ether Synthesis ◽  
Special Case ◽  
General Method ◽  
Episulfonium Ion

A general method for the formation of the cyclic ethers 9, 10, 13, 14, 16, and 28 and the lactone 30 is described. The procedure employs benzenesulfenyl chloride prepared insitu in acetonitrile and N,N-diisopropylethylamine to generate a thiiranium (episulfonium) ion intermediate from which the cyclic products arise by internal nucleophilic displacement. In the special case of the norbornene alcohols 1 and 2 the oxetanes 5 and 6 are formed by intramolecular sulfenate ester cycloaddition.

Participation of 19-substituents in electrophilic additions to 6,7-unsaturated 5α-cholestane and B-homo 5α-cholestane derivatives; A case of competition between the participation of an ambident neighboring group and external nucleophile attack

1980 ◽  
Vol 45 (2) ◽  
pp. 559-583 ◽  
Author(s):  
Pavel Kočovský ◽  
Ladislav Kohout ◽  
Václav Černý
Keyword(s):  
Perchloric Acid ◽  
Hydrobromic Acid ◽  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Neighboring Group ◽  
Acid Cleavage ◽  
Neighbouring Group Participation ◽  
Aqueous Perchloric Acid ◽  
The Difference ◽  
Electrophilic Additions

Hypobromous acid action upon the 6,7-unsaturated 19-substituted 5α-cholestans Va-Vc results in the formation of two types of products, the cyclic ethers IX as products of 5(O)n participation of the 19-substituent, and the bromohydrins X. All these compounds are formed from the 6α,7α-bromonium ions Va'-Vc'. Under the same conditions the B-homo-5α-cholestane derivatives VIIa-VIIc afforded solely the cyclic ethers XIV as products of 5(O)n participation of the 19-substituent in the cleavage of the bromonium ions VIIa'-VIIc'. Acid cleavage of the 6α,7α-epoxides VIb and VIc with aqueous perchloric acid or hydrobromic acid gave two types of products, i.e. the cyclic ethers XI and the diols XII or bromohydrines XIII. The cyclic ethers XI arise by 5(O)n participation of the 19-substituent. The B-homo-6α, 7α-epoxide VIIIc on cleavage with aqueous perchloric acid have solely the cyclic ether XVc and by treatment with hydrobromic acid VIIIc afforded the mixture of XVc, as the main product, and of the bromohydrin XVIc. Discussed is the similarity of the bromonium ion cleavage with the fission of the corresponding epoxides, the mechanism of these reactions and the difference in the behaviour of the isomeric olefins Ia-c, IIIa-c, Va-c and VIIa-c and epoxides IIb,c, IVb,c, VIb,c and VIIIb,c. The competition between ambident neighbouring group participation and external nucleophile attack is discussed as well as the dependence of the products ratio on the nucleophilicity of the attacking species.

A mild heteroatom (O-, N-, and S-) methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2 combination

Synthesis ◽  
2022 ◽  
Author(s):  
Yu Tang ◽  
Biao Yu
Keyword(s):  
Cost Efficiency ◽  
Room Temperature ◽  
High Efficiency ◽  
Attractive Alternative ◽  
Indole Derivatives ◽  
Trimethyl Phosphate ◽  
Environmental Friendly ◽  
Operational Simplicity

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2 combination has been developed, which proceeds in DMF, or water, or under neat conditions at 80 oC or at room temperature. A series of O-, N- and S-nucleophiles, including phenols, sulfonamides, N-heterocycles such as 9H-carbazole, indole derivatives, 1,8-naphthalimide, and aryl/alkyl thiols are suitable substrates of this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmental friendly nature of this protocol make it an attractive alternative to the conventional base prompted heteroatom methylation procedures.

scholarly journals Thioether-Catalysed Tandem Synthesis of Furans and Cyclic Ethers or Lactones

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1358-1362 ◽  
Author(s):  
J. Clark ◽  
Verena Klaus
Keyword(s):  
Carboxylic Acid ◽  
Cyclic Ether ◽  
Single Step ◽  
Cyclic Ethers ◽  
The Creation ◽  
Tandem Synthesis

Acyclic conjugated ynenediones tethered to an alcohol or carboxylic acid are converted into furanyl-substituted cyclic ethers or lactones in a single step by treatment with the tetrahydrothiophene. Modest levels of diastereocontrol can be achieved in some cases where the presence of a substituent on the tether results in the creation of a second stereogenic centre upon formation of the cyclic ether or lactone.

scholarly journals C(sp3)-H alkenylation promoted by uranyl cation as a visible-light photocatalyst

2021 ◽  
Vol 2079 (1) ◽  
pp. 012020
Author(s):  
Zhiyu Feng
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Bond Formation ◽  
Cyclic Ether ◽  
Hydrogen Atom Transfer ◽  
Cyclic Ethers ◽  
Atom Transfer ◽  
Target Product ◽  
Visible Light Photocatalyst ◽  
Uranyl Cation

Abstract The alkenylation of cyclic ethers with β-nitroalkenes using uranyl cation as a photocatalyst is reported. Previous studies revealed the feasibility of incorporating organic photocatalyst in the visible light mediated alkenylation, while the uranyl cation serves as an alternative photocatalyst candidate successfully accomplish this transformation through a different pathway. The reaction features the direct hydrogen atom transfer (HAT) process to activate alpha C(sp3)-H of cyclic ether, and consequently cyclic ether is coupled with β-nitroalkene to give the target product with F-selectivity through C-C bond formation.

scholarly journals A Potentially Useful Procedure for Conversion of Ethers to Esters

2021 ◽  
Vol 3 (1) ◽  
Author(s):  
Li H ◽  
Mark Z ◽  
Graylion M ◽  
Shen T
Keyword(s):  
Building Blocks ◽  
Cyclic Ether ◽  
Gas Chromatography Mass Spectrometry ◽  
High Yield ◽  
Infrared Spectrometry ◽  
Cyclic Ethers ◽  
Efficient Procedure ◽  
Nuclear Magnetic Resonance Spectrometry ◽  
Magnetic Resonance Spectrometry ◽  
Reaction Processes

This communication reports a catalytic system for transformation of ethers into their corresponding esters, especially for cyclic ethers. This efficient procedure was developed as part of our efforts to synthesize nucleoside building blocks and their derivatives. Gas Chromatography-Mass Spectrometry (GC-MS) monitored the reaction processes, Nuclear Magnetic Resonance Spectrometry (NMR), and Infrared Spectrometry (IR) were used to verify the structure of the products. The conversions of Tetrahydrofuran (THF) and other cyclic ether into lactones were accomplished in high yield, over 95%. This approach could be extended too many types of ethers to produce directly corresponding esters simply. Four representatives of ethers were investigated. Cyclic ethers have the higher yields. Linear ethers gave lower yields. The reaction on methoxylcarbon or methyl ether carbon was not observed. The reacted catalyst can be reused over several times. For each reusing, only drops of sulfuric acid need to be added. Nevertheless, the asymmetric ethers selectivity needs to be addressed in future studies.

scholarly journals Polymerization of Cyclic Ethers Initiated by the Reaction of Cyclic Ether with Hexafluoropropylene Oxide.

2002 ◽  
pp. 365-369 ◽  
Author(s):  
Yasuyuki MASUBUCHI ◽  
Tokio HAGIWARA ◽  
Youichi IKEGAYA ◽  
Seiji KAWATA ◽  
Noriyuki YONEZAWA
Keyword(s):  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Hexafluoropropylene Oxide

scholarly journals A New Variant of Fused Cyclic Ether Synthesis Based on Ireland-Claisen Rearrangement and RCM

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Daisuke Domon ◽  
Kenshu Fujiwara ◽  
Natsumi Kawamura ◽  
Ryo Katoono ◽  
Hidetoshi Kawai ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Claisen Rearrangement ◽  
Cyclic Ether ◽  
Reaction Sequence ◽  
New Variant ◽  
Ether Synthesis

A new variant of fused cyclic ether synthesis based on Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement and ring-closing olefin metathesis (RCM) was developed. The Ireland-Claisen rearrangement of a ( Z)-3-alkoxyprop-2-en-1-yl glycolate ester having a cyclic ether on the oxygen at C3 of the ( Z)-prop-2-en-1-yl group stereoselectively produced an anti-α,β-dialkoxyester which was successfully transformed to a fused bicyclic ether via a reaction sequence including RCM.

Metal-Free Visible-Light-Promoted C(sp3)–H Functionalization of Aliphatic Cyclic Ethers Using Trace O2

2021 ◽  
Author(s):  
Ben Niu ◽  
Bryan G. Blackburn ◽  
Krishnakumar Sachidanandan ◽  
Maria Victoria Cooke ◽  
Sébastien Laulhé
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Cyclic Ethers ◽  
Metal Free ◽  
Bond Forming

Presented is a light-promoted C–C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions...

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