Synthesis of 2-Alkylcyclohexanones Using Solvent-free Conditions and Microwave Technology
An expeditious solvent-free route to 2-alkylcyclohexanones from 2-ethoxycarbonylcyclohexanone is described via a solid-liquid phase transfer catalysed alkylation using ButOK as base and Aliquat 336 as catalyst and a LiBr-H2O-NBu4Br induced dealkoxycarbonylation under microwave activation in a focused open-vessel Maxidigest system.Yields were >/= 75percent over two steps.
Barnier, Jean Pierre,Loupy, Andre,Pigeon, Philippe,Ramdani, Mohamed,Jacquault, Patrick
p. 397 - 398
(2007/10/02)
Electroorganic Chemistry. 124. Electroreductive Intramolecular Coupling of α-(ω-Bromoalkyl) β-Keto Esters
Intramolecular coupling occurs when cyclic α-(bromomethyl) β-keto esters are electrochemically reduced in the presence of trimethylsilyl chloride and one-carbon ring-enlarged products are obtained in reasonable yields.Electroreduction of α-(γ-bromopropyl) β-keto esters also affords the corresponding five-membered cyclized products and/or the corresponding ring-opened compounds.The ease of ring opening of the cyclized products is highly influenced by their stereoconfiguration.Electroreduction of α-(β-bromoethyl) β-keto ester gives the product formed by the reductive elimination of the bromoethyl group whereas α-(δ-bromobutyl) β-keto ester yields the product of the reductive elimination of bromine.This electroreductive intramolecular coupling is initiated by the reduction of the carbon-bromine bond and proceeds through a carbanion intermediate.
A novel free radical initiated ring expansion of haloalkyl β-keto esters is described.Following alkylation of the β-keto ester with the appropriate dihalide, the resulting halide is treated at reflux with tri-n-butyltin hydride.Rearrangement to the homolo
Dowd, Paul,Choi, Soo-Chang
p. 77 - 90
(2007/10/02)
Free Radical Ring Expansion by Three and Four Carbons
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Dowd, Paul,Choi, Soo-Chang
p. 6548 - 6549
(2007/10/02)
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