Synthese und chemische Eigenschaften heterocyclischer Tetracyanodimethane eines heterocyclischen N,N′‐Dicyanodiimins sowie von voll substituierten monocyclischen Tetracyanodimethanen

Abstract

Syntheses and Chemical Properties of Heterocyclic Tetracyanodimethanes of a Heterocyclic N,N′‐Dicyanodiimine and of Fully Substituted Monocyclic TetracyanodimethanesIn the presence of different bases, 4,8‐diethoxy‐3H,7H‐benzo[1,2‐c:4,5‐c′]diisoxazole‐3,7‐dione (3) reacts with malonodinitrile or β‐oxobenzenepropanenitrile to the coloured salts 4a,b and 5, respectively, which are alkylated to the tetracyanoquinodimethane‐like heterocycles 2a,b and to the bis [benzoyl(cyano)methylidene]‐substituted heterocycle 6 (Scheme 1). Hydrogenation of 2a,b affords the fully substituted 7a,b, and with 2‐(1,3‐dithiol‐2‐ylidene)‐1,3‐dithiole, 2a gives the 1:1 charge‐transfer complex 8. Heterocyclic quinone 9 is transformed to the monocyarioimino derivative 10, and 3 reacts with cyanamide and NaH to the N,N′‐dicyanodiimine salt 12.