22665-14-1Relevant academic research and scientific papers
Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals
Ramdular, Amanda,Woerpel, K. A.
, (2020/06/08)
Neighboring-group participation of an ester enabled stereocontrol in substitution reactions of acyclic acetals. The ester group formed a trans-fused dioxolenium ion intermediate, which underwent a substitution reaction at the acetal carbon atom to afford the product with high diastereoselectivity. Neighboring-group participation was confirmed by isolating dioxolane products resulting from nucleophilic addition at C-2 of a 1,3-dioxolenium ion intermediate. Using a pivaloate ester as the participating group in combination with strong nucleophiles produced substitution products with diastereoselectivities of ≥90:10.
Absolute reactivity of arylallyl carbocations
Hallett-Tapley, Geniece,Cozens, Frances L.,Schepp, Norman P.
experimental part, p. 343 - 348 (2010/04/30)
A series of α-vinyl arylmethyl cations were generated and studied using nanosecond laser flash photolysis. Rate constants for the decay of the substituted α-vinyl arylmethyl cations were determined under solvolytic conditions in pure solvents and solvent
