ChemInform Abstract: NUCLEOPHILIC RING OPENING OF EPOXIDES BY CARBANIONS. NOVEL FORMATION OF CYCLOPROPANE DERIVATIVES IN A NONPOLAR SOLVENT

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.

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ChemInform Abstract: Aminopropyl Silica Gel Supported Iodine as Catalyst in Nucleophilic Ring Opening of Epoxides and Episulfides.

ChemInform ◽

10.1002/chin.200236044 ◽

2010 ◽

Vol 33 (36) ◽

pp. no-no

Author(s):

B. Tamami ◽

N. Iranpoor ◽

H. Mahdavi

Keyword(s):

Silica Gel ◽

Ring Opening ◽

Ring Opening Of Epoxides ◽

Nucleophilic Ring Opening

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Electrophilic Ring Opening of Small Heterocycles

Synthesis ◽

10.1055/s-0036-1589102 ◽

2017 ◽

Vol 49 (24) ◽

pp. 5307-5319 ◽

Cited By ~ 29

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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