90496-77-8Relevant academic research and scientific papers
REACTIVITE DE LITHIENS DERIVES D'ETHERS DE LA CYANHYDRINE DU BENZALDEHYDE VIS-A-VIS D'α-ENONES CYCLIQUES
Seuron, Nadine,Seyden-Penne, Jacqueline
, p. 635 - 640 (2007/10/02)
Conjugate addition of reagent 1A to 2-cyclohexenone 3 can be realized in THF-HMPT, so that one-pot conjugate addition - CH3I enolate trapping, leading to trans 2-methyl 3-benzoylcyclohexanone 17 can be easily performed.From isophorone 4 and Δ1(9)-2-octalone 5, 1,4-addition under kinetic control is observed in THF.In the presence of HMPA, the reaction is under thermodynamic control.At low temperatures enolate 19a is in equilibrium with 1A and 4; from 4 at 0 deg C or 5 at -65 deg C or at 0 deg C, the equilibrium lies on the side of starting materials.No reaction between 1A and 6 takes place in any solvent.The reaction of 1B and isophorone 4 in THF leads to 1,2-addition under kinetic control and to 1,4-addition under thermodynamic control.In THF-HMPT, retro-Michael addition is observed.However, 1,2-addition takes place in THF to 6. The different results are interpreted in terms of interplay of ion-pairing, steric decompression and steric hindrance to 1,4-addition as well as the possibility of participation of the Li cation for 1,2-addition.
ADDITION CONJUGUEE D'EQUIVALENTS D'ACYLES AUX CYCLOHEXEN-2 ONES ET A LA Δ1(9) OCTALONE-2 : SYNTHESE DE DICETONES 1-4.
Seuron, Nadine,Wartski, Lya,Seyden-Penne, Jacqueline
, p. 2175 - 2178 (2007/10/02)
The synthesis of 3-acetylcyclohexanones 11, 12, 13 has been realized by conjugate addition of lithiated cyanohydrin ether 1a to 2-cyclohexanones 2, 3, 4 in THF-HMPA, even if 3-substituted. 3-benzoylcyclohexanones 14, 15, 16 are obtained from 1b and 2, 3,
