Free-Radical Chemistry of Imines Journal Articles

abstract

• 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.

authors

• Tomaszewski, MJ
• Warkentin, J
• Werstiuk, Nick Henry

status

• published 

publication date

• 1995

has subject area

• 03 Chemical Sciences (FoR)
• General Chemistry (Science Metrix)

published in

• Australian Journal of Chemistry  Journal

keywords

• ALDIMINES
• ARRHENIUS PARAMETERS
• AZO GROUP
• CYCLIZATION
• Chemistry
• Chemistry, Multidisciplinary
• MECHANISM
• Physical Sciences
• RATE CONSTANTS
• REACTIVITY
• REGIO-SELECTIVITY
• RING-CLOSURE
• STEREO-SELECTIVITY
• Science & Technology

Digital Object Identifier (DOI)

• 10.1071/ch9950291

start page

• 291

end page

• 291

volume

• 48

issue

• 2