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Synthese und chemische Eigenschaften heterocyclischer Tetracyanodimethane eines heterocyclischen N , N ′‐Dicyanodiimins sowie von voll substituierten monocyclischen Tetracyanodimethanen
Author(s) -
Neidlein Richard,
Bischer Alfred
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730718
Subject(s) - chemistry , medicinal chemistry , derivative (finance) , alkylation , tetracyanoquinodimethane , salt (chemistry) , quinone , stereochemistry , organic chemistry , molecule , catalysis , financial economics , economics
Syntheses and Chemical Properties of Heterocyclic Tetracyanodimethanes of a Heterocyclic N , N ′‐Dicyanodiimine and of Fully Substituted Monocyclic Tetracyanodimethanes In 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.