Publication

Chasing an Elusive Alkoxide: Attempts to Synthesize [OC(tBu)(CF3)2]−

Rosario Scopelliti, Lutz Müller
2006
Journal Articles

Abstract

The synthesis of the alkoxide [OC(tBu)(CF3)2]− by the reaction of tBuM-reagents (M = Li; MgX) with hexafluoroacetone was attempted. This alkoxide was anticipated to be a good building block for novel weakly coordinating anions. However, in all attempted syntheses - also supported by theoretical DFT calculations - it was shown that [H]− addition is favored over [tBu]− addition. Thus compounds like [(Li(OC(H)(CF3)2]4·2Et2O (1) and (CF3)2(H)COMgCl·(OEt2)2 (4) were formed. An unexpected result was the formation of (THF)3LiO(CF3)2OC(H)(CF3)2(2), an addition compound built from [(CF3)2C(H)O]− and hexafluoroacetone. The alkoxy-alkoxide 2 could be useful for further applications.

Official source

https://infoscience.epfl.ch/entities/publication/2d099561-0898-4683-8d04-8b3a9a965b89

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Rosario Scopelliti, Lutz Müller
2006
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/2d099561-0898-4683-8d04-8b3a9a965b89

About this result

Related concepts (28)

Addition reaction

In organic chemistry, an addition reaction is an organic reaction where two or more molecules combine to form a larger one (the adduct). Addition reactions are limited to chemical compounds that have multiple bonds, such as molecules with carbon–carbon double bonds (alkenes), or with triple bonds (alkynes), and compounds that have rings, which are also considered points of unsaturation. Molecules containing carbon—hetero double bonds like carbonyl () groups, or imine () groups, can undergo addition, as they too have double-bond character.

Michael addition reaction

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

Chemical reaction

A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive elements where both electronic and nuclear changes can occur.

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