13366-92-2Relevant academic research and scientific papers
Electroorganic Chemistry. 124. Electroreductive Intramolecular Coupling of α-(ω-Bromoalkyl) β-Keto Esters
Shono, Tatsuya,Kise, Naoki,Uematsu, Nobuyuki,Morimoto, Shinji,Okazaki, Eiichi
, p. 5037 - 5041 (2007/10/02)
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.
Magnesium-Induced Cyclizations of 2-(3-Iodopropyl)cycloalkanones. A Cyclopentane Annelation Method
Crandall, Jack K.,Magaha, H. Steve
, p. 5368 - 5371 (2007/10/02)
A process for the stereoselective construction of a cyclopentane ring onto a preexisting cycloalkanone is developed. 2-(3-Iodopropyl)cycloalkanones, obtained by known methods from the parent cyclic ketones, were converted to bicycloalkan-1-ols in moderate to good yields by magnesium in THF.This cyclization shows a large preference for formation of the cis compounds.Attempts to extend this reaction to the formation of six- and seven-membered rings were largely unsuccessful.
13C NMR and Force Field Investigations of Hydrindane Conformations
Schneider, Hans-Joerg,Nguyen-Ba, Nghe
, p. 38 - 41 (2007/10/02)
13C NMR shifts of trans- and cis-annelated bicyclononanes with substituents R in position 8 (R = H, OH, Cl, Br) and 1-hydroxy derivatives were analysed on the basis of force field calculated torsional angles using Allinger's MM1 program.Schielding increments for the 6 membered ring agree with corresponding cyclohexane values within +/-0.8 ppm maximal deviation. 13C NMR line shape analysis with cis-hydrindane between 148 and 180 K yielded ΔH* = 37.0 +/- 0.4 kJ mol-1 and ΔS* = 28 J mol-1 K-1 for the topomerization.The force field calculated reaction profile showed ΔH* = 37 kJ mol-1, in close agreement.
