142387-83-5Relevant academic research and scientific papers
Rate constants for aryl radical cyclization of aldimines: Synthesis of tetrahydroisoquinolines by fast 6-endo closures to carbon
Tomaszewski,Warkentin
, p. 2123 - 2126 (1992)
Aryl radicals cyclize to an imino functional group in a competition involving 6-endo closure to C and 5-exo closure to N. there is a large 6-endo preference forming tetrahydroisoquinolinyl radicals with k(6-endo) (80°C) > 108 s-1.
Free-Radical Chemistry of Imines
Tomaszewski, Miroslaw J.,Warkentin, John,Werstiuk, Nick H.
, p. 291 - 322 (2007/10/02)
Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group.When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated.However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines.Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered.Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.
