ChemInform Abstract: SUBSTITUTION OF NITRILE GROUPS IN A DICYANOMETHYLENE FRAGMENT

Abstract

Die aus Tetracyanchinodimethan unter der Einwirkung 4‐substituierter Aniline entstehenden Verbindungen (I) reagieren mit prim. und sek. aliphatischen Aminen unter Substitution einer CN‐Gruppe und Bildung der Chinodimethane (II); intermediär treten im Reaktionsgemisch 1,6‐Addukte auf, die sich UV‐ und VIS‐spektrometrisch nachweisen lassen.

Recent Heterocyclic Compounds from (1,3‐Dioxo‐2,3‐dihydro‐1H‐inden‐2‐ylidene)propanedinitrile

“…Its EA is 2.45 eV, as compared with 2.75 and 2.85 eV for tetracyanoethylene 2 and tetracyanoquinodimethane 9 , respectively . …”

“…Chatterjee and Bespalov prepared CNIND 1 from indane‐1,2,3‐trione and malononitrile. CNIND 1 has also been synthesized from the reaction of indane‐1,3‐dione 10 with TCNE 2 (Scheme ).…”

Dicyanomethylene compounds and heterocyclization of substituted carbohydrazides

“…In organic π‐acceptors containing dicyanomethylene groups such as ethenetetracarbonitrile and (1,3‐dioxo‐2,3‐dihydro‐1 H ‐inden‐2‐ylidene)propanedinitrile ( 2 ), the nitrile groups can be substituted by the nucleophilic nitrogen atom of primary aromatic [1–3] and secondary aliphatic amines [4, 5]. Tertiary aromatic amines (like N,N ‐dimethylaniline) are prone to attack to the CC double bond of 2 with their para ‐position, followed by release of HCN [3, 6–10]. By reaction of acceptor 2 with tertiary cyclic amines, one can generate the iminium ions and formation of the α‐cyanated amines [11].…”