128749-55-3Relevant academic research and scientific papers
Stereochemistry of the Oxidation of Imines Derived from Substituted Cyclohexanones: Axial vs Equatorial Attack and Evidence for Delivery by an Adjacent Hydroxyl Group
Wang, Yuguang,Chackalamannil, Samuel,Aube, Jeffrey
, p. 5120 - 5126 (2000)
A set of conformationally biased imines derived from substituted cyclohexanones and benzylamine or diphenylmethylamine, respectively, were oxidized to the corresponding oxaziridines. The structures of the oxaziridines were determined via NMR comparison of two series of differently N-substituted oxaziridines. Thus, those compounds having an axially disposed nitrogen substituent displayed an upfield-shifted axial proton in a 1,3-relationship to the oxaziridine nitrogen in the N-diphenylmethyl series relative to the N-benzyl compounds. Analysis of the products obtained from these reactions suggests that (1) adjacent hydroxyl groups favor syn oxidant addition and (2) imines containing adjacent methoxy groups preferentially undergo attack anti to the resident alkoxy substituent.
Torsional, rotor, and electronic effects in 4-tert-butylmethylenecyclohexane epoxidations and osmylations
Vedejs,Dent III,Kendall,Oliver
, p. 3556 - 3567 (2007/10/03)
The axial epoxidation preference for 2-substituted 4-tert-butylmethylenecyclohexanes is attributed to a combination of small effects, including existing bond torsion and rotor effects. Contributions from developing bond torsion are smaller and may be negl
