A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1'-binaphthalene- 2,2'-diamines (BINAMs)
A facile and moderately functional-group-tolerant synthetic method for the preparation of 7,8-diaza[5]helicenes has been developed. It comprises of an oxidative ring-closing process of 1,1'-binaphthalene-2,2'-diamine (BINAM) derivatives with a chlorinecontaining oxidant (t - BuOCl) in the presence of a base (2,6-lutidine). In addition the basic physicochemical properties of newly synthesized compounds have been investigated.
Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) via C-C bond cleavage and nitrogen migration: A versatile synthesis of U-shaped azaacenes
An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′- diamines (BINAMs) that involves the cleavage of a strong C-C single bond of the binaphthalene unit and the nitrogen migration has been discovered. The unprecedented rearrangement enables access to a series of U-shaped azaacenes otherwise difficult to prepare in a selective manner by classical methods. Moreover, physicochemical properties of the unique azaacenes have been comprehensively investigated. This journal is the Partner Organisations 2014.