Nucleophilic Ring Opening of Epoxides by Organolithium Compounds: Ab Initio Mechanisms

1994 ◽  
Vol 116 (6) ◽  
pp. 2508-2514 ◽  
Author(s):  
Sjoerd Harder ◽  
Joop H. van Lenthe ◽  
Nicolaas J. R. van Eikema Hommes ◽  
Paul v. R. Schleyer
Keyword(s):  
Ab Initio ◽  
Ring Opening ◽  
Organolithium Compounds ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Nucleophilic ring-opening of epoxides: trends in β-substituted alcohols synthesis

2018 ◽  
Vol 15 (9) ◽  
pp. 2033-2081 ◽  
Author(s):  
Mehdi Fallah-Mehrjardi ◽  
Ali Reza Kiasat ◽  
Khodabakhsh Niknam
Keyword(s):  
Ring Opening ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2214-2220 ◽  
Author(s):  
Monika Stefaniak ◽  
Jarosław Romański
Keyword(s):  
Click Chemistry ◽  
Ring Opening ◽  
Facile Synthesis ◽  
Step Procedure ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Thiacrown Ethers ◽  
Hydroxy Groups ◽  
First Time ◽  
Nucleophilic Ring Opening

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson’s birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.

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

Ab initio investigation on nucleophilic ring opening of 1,3,2-oxathiaphospholane: nucleophilic substitution at phosphorus coupled with pseudorotation

1996 ◽  
Vol 263 (5) ◽  
pp. 691-696 ◽  
Author(s):  
Tadafumi Uchimaru ◽  
Wojciech J. Stec ◽  
Seiji Tsuzuki ◽  
Takuji Hirose ◽  
Kazutoshi Tanabe ◽  
...  
Keyword(s):  
Ab Initio ◽  
Nucleophilic Substitution ◽  
Ring Opening ◽  
Nucleophilic Ring Opening
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