13366-91-1Relevant articles and documents
Magnesium-Induced Cyclizations of 2-(3-Iodopropyl)cycloalkanones. A Cyclopentane Annelation Method
Crandall, Jack K.,Magaha, H. Steve
, p. 5368 - 5371 (1982)
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.
