A Further Study of the Course of Ring-opening of Unsymmetrical Epoxides with Nucleophilic Reagents

1953 ◽  
Vol 75 (2) ◽  
pp. 294-296 ◽  
Author(s):  
George D. Zuidema ◽  
Paul L. Cook ◽  
Gerrit Van Zyl
Keyword(s):  
Ring Opening ◽  
Nucleophilic Reagents

The reactions of isothiazolium salts with selected nucleophilic reagents. The preparation of thieno[2,3-c]isothiazolium salts

1977 ◽  
Vol 55 (7) ◽  
pp. 1123-1128 ◽  
Author(s):  
David M. McKinnon ◽  
Mohammed E. R. Hassan ◽  
Mohinder Chauhan
Keyword(s):  
Ring Opening ◽  
Nucleophilic Attack ◽  
Isothiazolium Salts ◽  
Thiophene Derivatives ◽  
Nucleophilic Reagents

Isothiazolium salts react with a number of carbanions by attack on sulfur. Thiophene derivatives, formed by ring opening and recyclization, are often products but with cyclopentadiene, pseudoazulene products are obtained. 3-Amino-2-acylthiophenes, prepared by suitable nucleophilic attack, are synthetic precursors of thieno[2,3-c]isothiazolium salts

scholarly journals Regio- and stereoselective synthesis of new diaminocyclopentanols

2014 ◽  
Vol 10 ◽  
pp. 2513-2520 ◽  
Author(s):  
Evgeni A Larin ◽  
Valeri S Kochubei ◽  
Yuri M Atroshchenko
Keyword(s):  
Nitrogen Atom ◽  
Ring Opening ◽  
Stereoselective Synthesis ◽  
Alternative Pathway ◽  
Acid Catalyst ◽  
Epoxide Ring ◽  
Optimal Conditions ◽  
Epoxide Ring Opening ◽  
Lewis Acid Catalyst ◽  
Nucleophilic Reagents

The optimal conditions for regio- and stereoselective epoxide ring opening of N,N-disubstituted 1,2-epoxy-3-aminocyclopentanes by different nucleophilic reagents have been developed. The substituents on the nitrogen atom in the epoxide precursor and the orientation of the oxirane ring are crucial for the reaction outcome. Thus, treatment of (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzylamino)cyclopentane (3b) with amines gave a mixture of C1 and C2 regioadducts, while the use of (1RS,2SR,3SR)-1,2-epoxy-3-(N-benzyl-N-methylamino)cyclopentane (3a) led ultimately to C1 adducts. Base-catalyzed aminolysis of epoxides 6a,b afforded mainly C1 adducts 13a,b arising from trans-diaxal opening of the epoxide ring. Using a Lewis acid catalyst, epoxides 6a,b were transformed into diaminocyclopentanols 14a,b via an alternative pathway involving the formation of aziridinium intermediate 17.

The Course of Ring Opening of Glycidyl Ethers with Nucleophilic Reagents

1953 ◽  
Vol 75 (20) ◽  
pp. 5002-5006 ◽  
Author(s):  
Gerrit Van Zyl ◽  
George D. Zuidema ◽  
John F. Zack ◽  
Paul B. Kromann
Keyword(s):  
Ring Opening ◽  
Glycidyl Ethers ◽  
Nucleophilic Reagents

Regiodirectivity of ring-opening of 2,3-epoxyperfluoroalkanes by nucleophilic reagents

1992 ◽  
Vol 58 (2-3) ◽  
pp. 308
Author(s):  
A.Ya. Zapevalov ◽  
L.V. Saloutina ◽  
T.I. Filyakova ◽  
M.I. Kodess
Keyword(s):  
Ring Opening ◽  
Nucleophilic Reagents

Amino-functional polyethers: versatile, stimuli-responsive polymers

2020 ◽  
Vol 11 (24) ◽  
pp. 3940-3950 ◽  
Author(s):  
Patrick Verkoyen ◽  
Holger Frey
Keyword(s):  
Ring Opening ◽  
Review Article ◽  
Stimuli Responsive ◽  
New Class ◽  
Stimuli Responsive Polymers ◽  
Responsive Polymers

Amino-functional polyethers have emerged as a new class of “smart”, i.e. pH- and thermoresponsive materials. This review article summarizes the synthesis and applications of these materials, obtained from ring-opening of suitable epoxide monomers.

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