143447-58-9Relevant academic research and scientific papers
Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions
Negri, Joanna T.,Paquette, Leo A.
, p. 8835 - 8841 (1992)
The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a domi
Intramolecular Meta Photocycloaddition of Conformationally Restrained 5-Phenylpent-1-enes. Part I: Bichromophoric Cyclohexane Derivatives
Barentsen, Helma M.,Talman, Edger G.,Piet, Dennis P.,Cornelisse, Jan
, p. 7469 - 7494 (2007/10/02)
The cis isomers of 1-allyl-2-phenycyclohexane and 1-benzyl-2-vinylcyclohexane yield predominantly 1,3 addition, while the trans isomers show a high selectivity for 2,6 addition, which is explained by steric interactions.Introduction of a third substituent, OH or OCH3, on the alkenyl substituted carbon of the cyclohexane ring gives almost exclusively 1,3 addition.This can mostly be explained in terms of more steric hindrance in the conformations leading to 2,6 addition.From the results described it can be concluded that for 2,6 additon two conformations are available, while the energy difference between the 1,3 conformations is much larger and therefore a completely stereoselective 1,3 addition is found (except for 6).
