A SIMPLE SYNTHESIS OF 4,5-DISUBSTITUTED 1,2-DICYANOBENZENES AND 2,3,9,10,16,17,23,24-OCTASUBSTITUTED PHTHALOCYANINES

4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propyl...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 2; pp. 194 - 196
Main Authors WOHRLE, D, ESKES, M, SHIGEHARA, K, YAMADA, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 1993
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CELLS
BASES
INDUSTRY
POLYMER
PHTHALONITRILE
ELECTRODES
SCIENCE
Online AccessGet more information

Cover

More Information
Summary:4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propylthio)-1,2-dicyanobenzenes 6 which were converted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in high yields to octasubstituted phthalocyanines (tetrabenzoporphyrazines) 7. Some compounds 7 contain eight free phenolic, carboxylic acid or pyridyl groups.
ISSN:0039-7881
DOI:10.1055/s-1993-25825