31062-13-2Relevant academic research and scientific papers
Asymmetric Lewis Acid-Catalyzed Diels-Alder Reactions of α,β-Unsaturated Ketones and α,β-Unsaturated Acid Chlorides
Hawkins, Joel M.,Nambu, Mitch,Loren, Stefan
, p. 4293 - 4295 (2003)
(Equation presented) Conformational analysis, van der Waals attractions, and transition structure calculations are combined to design an asymmetric Lewis acid-catalyzed Diels-Alder reaction for simple acyclic α,β-unsaturated ketones and α,β-unsaturated acid chlorides, giving up to 83 and 92% ee, respectively. The two-point-binding chiral recognition mechanism, Lewis acid-Lewis base coordination with boron and a van der Waals attraction with the naphthyl group, uses the inherent enone unit of simple α,β-unsaturated carbonyl compounds, ending the need for auxiliary oxygen binding sites on the dienophile.
Electrochemical Reduction of exo-5-Acetyl-endo-6-trichloromethylbicyclohept-2-ene
Tsuboi, Sadao,Ishiguro, Yasuhiro,Takeda, Akira
, p. 830 - 832 (2007/10/02)
Electrochemical reduction of exo-5-acetyl-endo-6-trichloromethylbicyclohept-2-ene (2) using a mercury cathode gave chemoselectively either the corresponding monochloromethyl or dichloromethyl derivatives in high yields by selecting supporting electrolyte.The reduction of 2 using a lead cathode gave 2-acetyl-3-methylbicyclohepta-2,5-diene and cis-1-(4-vinyl-2-cyclopentenyl)-2-propane together wwith by-products.
PREPARATION DE THIOCETONES ACYCLIQUES α-INSATUREES. DIMERISATION REGIOSELECTIVE EN 4H-DITHIINE-1,3
Beslin, P.,Lagain, D.,Vialle, J.,Minot, C.
, p. 3839 - 3846 (2007/10/02)
α-Unsaturated acyclic thioketones 6 a-d were prepared by a retro-Diels-Alder reaction using flash thermolysis technique.They were detected at low temperature (blue coloured pyrolysate) but dimerize in solution as soon as the temperature rose to -60o (case 6 a-c) and -20o (case 6 d).The structure of 6 d was established by UV and NMR spectra taken at -60o.Dimeric products were proved to be 4H-1,3 dithiin by spectral data and by univocal synthesis of 7 c and 7 d from the corresponding monomeric ketone. 1-3 Dithiin 7 d was isomerized at 190o into the thermodynamic isomer (8).This observed orientation of dimerisation agrees with theorical results obtained from molecular frontier orbital calculations.
