Cyclohexenone synthesis - Organic Chemistry Portal
The use of allyl-palladium catalysis enables a one-step α,β-dehydrogenation of ketones via their zinc enolates. The optimized protocol utilizes commercially available Zn(TMP) 2 as base and diethyl allyl phosphate as oxidant, operates under salt-free conditions, and tolerates a diverse scope of cycloalkanones.
Cyclohexenone - Wikipedia
Cyclohexenone is a widely used building block in organic synthesis chemistry, as it offers many different ways to extend molecular frameworks. As an enone, cyclohexenone is easily adapted to Michael addition with nucleophiles (such as enolates or silyl enol ethers) or, it could be employed by a Diels-Alder reaction with electron-rich dienes.
Selective formation of enolates - Chemistry Stack Exchange
2023年10月16日 · The enone moiety in cyclohexenone 3 has strong conjugation between the carbonyl and the double bond owing to restricted rotation about the $\ce{C1-C2}$ bond. The methylene group is deprotonated kinetically. 2 Enones 1 and 2 have a degree of free rotation about their respective $\ce{C2-C3}$ bonds.
Stereospecific Synthesis of Cyclohexenone Acids by [3,3] …
Herein we report a modular synthetic method for the preparation of diaryl-substituted cyclohexenone acids starting from phenyl pyruvate and suitable enones. When the reaction is carried out in alkaline tert -butanol or toluene solutions in microwave-assisted conditions mainly anti configuration products are obtained with up to 86% isolated yield.
2007年1月8日 · When unsymmetrical carbonyl compounds are converted to their enolates under conditions that allow equilibrium to be established (high temperatures and weak bases) the enolate anion with the more highly substituted double bond is formed. This ion is the more stable of the two possible enolates and is called the thermodynamic enolate.
thermodynamic and kinetic enolates that would be obtained from 2-cyclohexenone. What conditions are most commonly used to generate each enolate? Deprotonation of a carbonyl compound to form an enolate may proceed under thermodynamic conditions such that the enolate products are in equilibrium.
Cyclohexenone - (Organic Chemistry) - Vocab, Definition
The presence of the carbonyl group and the carbon-carbon double bond in the cyclohexenone structure allows for the formation of an enolate ion, which is a key intermediate in aldol reactions. The enolate ion can act as a nucleophile and attack another carbonyl compound, leading to the formation of a new carbon-carbon bond and an $\alpha,\beta ...
Mechanistically, the reaction commences when an enolate tautomer of phenylpyruvic acid attacks the aromatic enone and forms a hemiketal intermediate (i, Figure 5). The reaction continues via oxy-Cope type [3,3]-sigmatropic rearrangement followed by H+ transfer, generating a diketone intermediate ii, which bears pyruvate acid and ketone ...
The Robinson annulation is an organic reaction used to convert a ketone and an α,β-unsaturated ketone to a cyclohexenone using base. The mechanism begins with deprotonation with the base of the α-hydrogen of the ketone to form an enolate. The enolate then does a 1,4 addition to the conjugated olefin
Vinylation of cyclohexanone enolates using vinyl ether-iron …
Vinylation of cyclohexanone enolates using vinyl ether-iron complexes. Diastereoselectivity of carbon-carbon bond formation. Tony C. T. Chang, Thomas S. Coolbaugh, Bruce M. Foxman, Myron. Rosenblum, N. Simms, and ; C. Stockman
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