Die Chemie des Tetracyanäthylens

The most convenient method for the preparation of tetracyanoethylene is to react dibromomalonitrile with copper powder in boiling benzene solution. The high melting tetracyanoethylene is a mild oxidizing agent and its double bond is highly electron deficient. Thus it acts as an electron acceptor, r...

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Main Author: R. Winkler
Format: Article
Language:deu
Published: Swiss Chemical Society 1962-11-01
Series:CHIMIA
Online Access:https://www.chimia.ch/chimia/article/view/8177
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author R. Winkler
author_facet R. Winkler
author_sort R. Winkler
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description The most convenient method for the preparation of tetracyanoethylene is to react dibromomalonitrile with copper powder in boiling benzene solution. The high melting tetracyanoethylene is a mild oxidizing agent and its double bond is highly electron deficient. Thus it acts as an electron acceptor, reacting with systems containing an excess of π-electrons, such as aromatic hydrocarbons, to form coloured charge transfer complexes. With 1,3-dienes, ketones with α-hydrogen atoms and reducing agents, it gives rise to addition products. With nucleophilic reagents such as alcohols, bases, aromatic hydrocarbons and heterocyclics rich in electrons, it undergoes substitution reactions, whereby one or two nitrile groups may be substituted. Subsequent reactions starting from these different products lead to new heterocyclic systems, strong acids, dyes, luminescent compounds and polymers for different technical applications.
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spelling doaj-art-179f7b882b07404cab498b77ccba2c5f2025-08-20T03:53:28ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241962-11-01161110.2533/chimia.1962.360Die Chemie des TetracyanäthylensR. Winkler0CIBA Aktiengesellschaft, Basel The most convenient method for the preparation of tetracyanoethylene is to react dibromomalonitrile with copper powder in boiling benzene solution. The high melting tetracyanoethylene is a mild oxidizing agent and its double bond is highly electron deficient. Thus it acts as an electron acceptor, reacting with systems containing an excess of π-electrons, such as aromatic hydrocarbons, to form coloured charge transfer complexes. With 1,3-dienes, ketones with α-hydrogen atoms and reducing agents, it gives rise to addition products. With nucleophilic reagents such as alcohols, bases, aromatic hydrocarbons and heterocyclics rich in electrons, it undergoes substitution reactions, whereby one or two nitrile groups may be substituted. Subsequent reactions starting from these different products lead to new heterocyclic systems, strong acids, dyes, luminescent compounds and polymers for different technical applications. https://www.chimia.ch/chimia/article/view/8177
spellingShingle R. Winkler
Die Chemie des Tetracyanäthylens
CHIMIA
title Die Chemie des Tetracyanäthylens
title_full Die Chemie des Tetracyanäthylens
title_fullStr Die Chemie des Tetracyanäthylens
title_full_unstemmed Die Chemie des Tetracyanäthylens
title_short Die Chemie des Tetracyanäthylens
title_sort die chemie des tetracyanathylens
url https://www.chimia.ch/chimia/article/view/8177
work_keys_str_mv AT rwinkler diechemiedestetracyanathylens