ChemInform Abstract: Palladium-Catalyzed Ring-Opening Reactions of 1-Acetyl-4-vinyl-2- azetidinones and 1-Sulfonyl-2-vinylazetidines. Role of Intramolecular Participation of Amide Anion.

ChemInform ◽  
2010 ◽  
Vol 26 (36) ◽  
pp. no-no
Author(s):  
A. SATAKE ◽  
H. ISHII ◽  
I. SHIMIZU ◽  
Y. INOUE ◽  
H. HASEGAWA ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed

Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion

Tetrahedron ◽  
1995 ◽  
Vol 51 (18) ◽  
pp. 5331-5340 ◽  
Author(s):  
Akiharu Satake ◽  
Hideo Ishii ◽  
Isao Shimizu ◽  
Yoichi Inoue ◽  
Hajime Hasegawa ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed

scholarly journals The preparation and properties of 1,1-difluorocyclopropane derivatives

2021 ◽  
Vol 17 ◽  
pp. 245-272
Author(s):  
Kymbat S Adekenova ◽  
Peter B Wyatt ◽  
Sergazy M Adekenov
Keyword(s):  
Ring Opening ◽  
Organic Molecules ◽  
Biological Importance ◽  
Ring Opening Reactions

Recently, the functionalization of organic molecules with fluorine substituents has grown rapidly due to its applications in such fields as medicine, agriculture or materials sciences. The aim of this article is to review the importance of 1,1-difluorocyclopropane derivatives in synthesis. It will examine the role of the fluorine substituents in both ring-forming and ring-opening reactions, as well as methods for obtaining difluorocyclopropanes as single enantiomers. Several examples are provided to highlight the biological importance of this class of compounds.

scholarly journals Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

2016 ◽  
Vol 12 ◽  
pp. 239-244 ◽  
Author(s):  
Michael Edmunds ◽  
Mohammed Abdul Raheem ◽  
Rebecca Boutin ◽  
Katrina Tait ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Optimal Conditions ◽  
Aryl Iodides ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed

Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl2(PPh3)2, ZnCl2, Et3N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained.

Norbornene in Organic Synthesis

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2799-2823 ◽  
Author(s):  
Jianhui Huang ◽  
Caifeng Li ◽  
Liu Liu ◽  
Xuegang Fu
Keyword(s):  
Ring Opening ◽  
Membered Ring ◽  
Ring Formation ◽  
Oxidation Reactions ◽  
Organic Transformations ◽  
Substitution Reactions ◽  
Reaction Conditions ◽  
Multistep Synthesis ◽  
Palladium Catalyzed

The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.1 Introduction2 Synthesis of Substituted Norbornenes2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed­ Reaction Conditions2.3 Alkylation of Norbornene2.4 Multistep Synthesis3 Synthesis of Substituted Norbornanes3.1 Three-Membered-Ring Formation3.2 Formation of Four-Membered Rings3.3 Five- and Six-Membered Ring Formation3.4 Syntheses of Difunctionalized Norbornanes4 Synthesis of Cyclopentanes4.1 Oxidation Reactions4.2 Ring-Opening Cross Metathesis (ROCM)4.3 Ring-Opening Metathesis Polymerization (ROMP)4.4 Palladium-Catalyzed Ring-Opening of Norbornene5 Norbornene-Mediated Reactions5.1 Palladium Insertion into Carbon–Halide Bonds5.2 Palladium Insertion into N–H and C–H Bonds5.3 Norbornene as Ligand in Mediated Reactions6 Conclusion

Palladium-Catalyzed Synthesis of Polysubstituted Pyrazoles by Ring-Opening Reactions of 2H-Azirines with Hydrazones

Synlett ◽  
2020 ◽  
Author(s):  
Jiaan Shao ◽  
Ke Shu ◽  
Wenteng Chen ◽  
Shuangrong Liu ◽  
Huajian Zhu ◽  
...  
Keyword(s):  
Ring Opening ◽  
Chemical Conversion ◽  
Alternative Route ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed ◽  
Plausible Mechanism

AbstractA palladium–catalyzed ring-opening reaction of 2H-azirines with hydrazones has been developed. This protocol provides an alternative route for the construction of various polysubstituted pyrazoles with a wide substrate scope. Moreover, a plausible mechanism is proposed for this reaction, which should further enrich the chemical conversion of 2H-azirines.

ChemInform Abstract: Regioselective Palladium-Catalyzed Ring-Opening Reactions of C1-Substituted Oxabenzonorbornadienes.

ChemInform ◽  
2015 ◽  
Vol 46 (10) ◽  
pp. no-no
Author(s):  
Mohammed Abdul Raheem ◽  
Michael Edmunds ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed

ChemInform Abstract: Regioselective Palladium-Catalyzed Ring-Opening Reactions of C1-Substituted Oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates.

ChemInform ◽  
2016 ◽  
Vol 47 (21) ◽  
Author(s):  
Michael Edmunds ◽  
Mohammed Abdul Raheem ◽  
Rebecca Boutin ◽  
Katrina Tait ◽  
William Tam
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed

Electrophilic Ring Opening of Small Heterocycles

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5307-5319 ◽  
Author(s):  
Chuan Wang
Keyword(s):  
Ethylene Oxide ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Nickel Titanium ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Small heterocycles, such as epoxides, aziridines, and ox­etanes are among the most useful building blocks in organic synthesis. Through electrophilic ring opening of these molecules, various electrophilic functional groups can be installed, which cannot be achieved via classic nucleophilic ring-opening reactions. In this review, the developments of electrophilic ring opening of small heterocycles are surveyed and organized according to the types of metal promoters.1 Introduction2 Electrophilic Ring Opening of Small Heterocycles Using Stoichiometric Metals2.1 Lithium-Mediated Electrophilic Ring Opening of Epoxides and Oxetanes2.2 Chromium-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.3 Tin-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.4 Samarium-Mediated Electrophilic Ring Opening of Vinyl and Alkynyl Epoxides2.5 Titanium-Mediated Electrophilic Ring Opening of Epoxides2.6 Platinum, Palladium, and Nickel-Mediated Electrophilic Ring Opening of 1,1-Dimethyl Ethylene Oxide3 Catalytic Electrophilic Ring Opening of Small Heterocycles3.1 Titanium-Catalyzed Electrophilic Ring Opening of Epoxides3.2 Palladium-Catalyzed Electrophilic Ring Opening of Vinyl and Alkynyl Small Heterocycles3.3 Iron-Catalyzed Electrophilic Ring Opening of Oxetanes3.4 Scandium-Catalyzed Electrophilic Ring Opening of Vinyl Epoxides3.5 Iridium-Catalyzed Electrophilic Ring Opening of 2-Methyl 2-Vinyl­oxiranes3.6 Nickel-Catalyzed Electrophilic Ring Opening of Epoxides and Aziridines3.7 Nickel–Titanium-Cocatalyzed Electrophilic Ring Opening of Epoxides4 Summary

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