Fluoro- and cyano-substituted 7,7,8,8-tetracyanoquinodimethans and intermediates thereto
Abstract
Abstract 7,7,8,8-TETRACYANOQUINODIMETHANS SUBSTITUTED WITH FLUORO OR CYANO GROUPS IN THE RING CAN BE MADE BY A THREESTEP PROCESS COMPRISING: (1) REACTING A SUBSTITUTED PARADIHALOBENZENE WITH A HYDROCARBYL MONO-SUBSTITUTED MALONONITRILE HAVING AT LEAST ONE ALIPHATIC HYDROGEN B TO THE CH(CN)2 GROUP, IN THE PRESENCE OF AN ALKALI METAL, AN ALKALINE EARTH METAL OR THEIR HYDRIDES; (2) THERMALLY DECOMPOSING THE INTERMEDIATE FORMED IN ( 1) TO A SUBSTITUTED DIHYDROTETRACYANOQUINODIMETHAN (STCNQH2); (3) OXIDIZING THE INTERMEDIATE STCNQH2 TO A SUBSTITUTED 7,7,8,8TETRACYANOQUINODIMETHAN, (STCNQ). THE COMPOUNDS (STNQH2) FORM COLORED SALTS WITH QUATERNARY AMMONIUM COMPOUNDS WHICH ARE USEFUL AS DYES. THE COMPOUNDS (STCNQ) FORM CHARGE-TRANSFER SALTS WITH CATIONS AND COMPLEXES WITH LEWIS BASES WHICH ARE USEFUL AS CHEMICAL REAGENTS, AS DYES OR PIGMENTS.
Inventors
- 👤 Elmore Louis Martin
Bibliographic Details
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