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...
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| Published in | Synthesis (Stuttgart) no. 2; pp. 194 - 196 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
STUTTGART
Thieme Medical Publishers
1993
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| Subjects | |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | SHIGEHARA, K ESKES, M YAMADA, A WOHRLE, D |
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| References | WOHRLE, D (WOS:A1989U938800005) 1989; 190 MOSER FH (WOS:A1993KN23400003.10) 1983; 1 WOHRLE, D (WOS:A1992HM21000002) 1992; 18 VANDERPOL, JF (WOS:A1990CH78600027) 1990; 23 KELLER, TM (WOS:A1980KC96700002) 1980 WOHRLE, D (WOS:A1983QA21500003) 1983; 50 MOHAMMED, MA (WOS:A1992HY24700022) 1992; 213 VILLINGER V (WOS:A1993KN23400003.19) 1909; 42 WOHRLE, D (WOS:A1989AY32200017) 1989; 19 COOK, MJ (WOS:A1988Q309000063) 1988 TOMODA, H (WOS:A1983QE74800017) 1983 LEVER ABP (WOS:A1993KN23400003.8) 1989 WOHRLE, D (WOS:A1991FD14700002) 1991; 3 GIROUDGODQUIN, AM (WOS:A1991FM11400003) 1991; 30 KANEKO, M (WOS:A1988M257700005) 1988; 84 WOHRLE, D (WOS:A1990CU93600013) 1990; 51 MOSER FH (WOS:A1993KN23400003.11) 1983; 2 PAWLOWSKI, G (WOS:A1980JQ10300004) 1980 COYLE, JD (WOS:A1985AAH7600019) 1985 SIMON J (WOS:A1993KN23400003.15) 1985 CROCKETT, GC (WOS:A1981LT36000005) 1981; 11 GIROUDGODQUIN AM (WOS:A1993KN23400003.4) 1991; 103 TOMODA, H (WOS:A1980KL24900024) 1980 SCHLETTWEIN, D (WOS:A1991EY68000049) 1991; 95 WOHRLE, D (WOS:A1988M030100045) 1988 SIEGL, WO (WOS:A1981NB70200026) 1981; 18 |
| References_xml | – volume: 84 start-page: 141 year: 1988 ident: WOS:A1988M257700005 article-title: POLYMER-COATED ELECTRODES - NEW MATERIALS FOR SCIENCE AND INDUSTRY publication-title: ADVANCES IN POLYMER SCIENCE contributor: fullname: KANEKO, M – volume: 51 start-page: 351 year: 1990 ident: WOS:A1990CU93600013 article-title: SYNTHESIS OF POSITIVELY CHARGED PHTHALOCYANINES AND THEIR ACTIVITY IN THE PHOTODYNAMIC THERAPY OF CANCER-CELLS publication-title: PHOTOCHEMISTRY AND PHOTOBIOLOGY contributor: fullname: WOHRLE, D – volume: 18 start-page: 1613 year: 1981 ident: WOS:A1981NB70200026 article-title: METAL-CHELATING 1,3-BIS(2'-PYRIDYLIMINO)ISOINDOLINES publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY contributor: fullname: SIEGL, WO – volume: 30 start-page: 375 year: 1991 ident: WOS:A1991FM11400003 article-title: METALLOMESOGENS - METAL-COMPLEXES IN ORGANIZED FLUID PHASES publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: GIROUDGODQUIN, AM – start-page: 549 year: 1988 ident: WOS:A1988M030100045 article-title: OCTABUTOXYPHTHALOCYANINE, A NEW ELECTRON-DONOR publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS contributor: fullname: WOHRLE, D – start-page: 2453 year: 1988 ident: WOS:A1988Q309000063 article-title: OCTA-ALKOXY PHTHALOCYANINE AND NAPHTHALOCYANINE DERIVATIVES - DYES WITH Q-BAND ABSORPTION IN THE FAR RED OR NEAR-INFRARED publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: COOK, MJ – start-page: 313 year: 1983 ident: WOS:A1983QE74800017 article-title: SYNTHESIS OF METALLOPHTHALOCYANINES FROM PHTHALONITRILE WITH STRONG ORGANIC-BASES publication-title: CHEMISTRY LETTERS contributor: fullname: TOMODA, H – volume: 103 start-page: 370 year: 1991 ident: WOS:A1993KN23400003.4 publication-title: ANGEW CHEM contributor: fullname: GIROUDGODQUIN AM – year: 1989 ident: WOS:A1993KN23400003.8 publication-title: PHTHALOCYANINES PROP contributor: fullname: LEVER ABP – start-page: 287 year: 1980 ident: WOS:A1980JQ10300004 article-title: SYNTHESIS AND PROPERTIES OF A NEW KIND OF ONE-DIMENSIONAL CONDUCTORS .4. A CONVENIENT SYNTHESIS OF OCTASUBSTITUTED PHTHALOCYANINES publication-title: SYNTHESIS-STUTTGART contributor: fullname: PAWLOWSKI, G – year: 1985 ident: WOS:A1993KN23400003.15 publication-title: MOL SEMICONDUCTORS contributor: fullname: SIMON J – volume: 23 start-page: 155 year: 1990 ident: WOS:A1990CH78600027 article-title: A POLYMER WITH THE MESOMORPHIC ORDER OF LIQUID-CRYSTALLINE PHTHALOCYANINES publication-title: MACROMOLECULES contributor: fullname: VANDERPOL, JF – start-page: 1277 year: 1980 ident: WOS:A1980KL24900024 article-title: SYNTHESIS OF PHTHALOCYANINES FROM PHTHALONITRILE WITH ORGANIC STRONG BASES publication-title: CHEMISTRY LETTERS contributor: fullname: TOMODA, H – volume: 2 year: 1983 ident: WOS:A1993KN23400003.11 publication-title: PHTHALOCYANINES contributor: fullname: MOSER FH – start-page: 121 year: 1985 ident: WOS:A1985AAH7600019 article-title: PHOTOCYCLIZATION OF N-(DIALKYLAMINOALKYL) AROMATIC 1,2-DICARBOXIMIDES - X-RAY MOLECULAR-STRUCTURE OF A STEREOISOMER OF 4-BENZYL-2-HYDROXY-3-PHENYL-4,6-DIAZATRICYCLO[6.4.0.02,6]DODECA-1(12),8,10-TRIEN-7-ONE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: COYLE, JD – volume: 95 start-page: 1748 year: 1991 ident: WOS:A1991EY68000049 article-title: LIGHT-INDUCED DIOXYGEN REDUCTION AT THIN-FILM ELECTRODES OF VARIOUS PORPHYRINS publication-title: JOURNAL OF PHYSICAL CHEMISTRY contributor: fullname: SCHLETTWEIN, D – volume: 213 start-page: 285 year: 1992 ident: WOS:A1992HY24700022 article-title: LANGMUIR-BLODGETT-FILMS OF PHTHALOCYANINE DERIVATIVES - MONOLAYER AND MULTILAYER FILMS PREPARED FROM PHTHALOCYANINE DERIVATIVES CONTAINING POLAR AND CATIONIC SUBSTITUENTS publication-title: THIN SOLID FILMS contributor: fullname: MOHAMMED, MA – volume: 1 year: 1983 ident: WOS:A1993KN23400003.10 publication-title: PHTHALOCYANINES contributor: fullname: MOSER FH – start-page: 613 year: 1980 ident: WOS:A1980KC96700002 article-title: SYNTHESIS OF PHTHALONITRILES BY NITRO DISPLACEMENT publication-title: SYNTHESIS-STUTTGART contributor: fullname: KELLER, TM – volume: 50 start-page: 45 year: 1983 ident: WOS:A1983QA21500003 article-title: POLYMER SQUARE-PLANAR METAL-CHELATES FOR SCIENCE AND INDUSTRY - SYNTHESIS, PROPERTIES AND APPLICATIONS publication-title: ADVANCES IN POLYMER SCIENCE contributor: fullname: WOHRLE, D – volume: 190 start-page: 961 year: 1989 ident: WOS:A1989U938800005 article-title: PHTHALOCYANINES ON MINERAL CARRIERS .4. LOW-MOLECULAR-WEIGHT AND POLYMERIC PHTHALOCYANINES ON SIO2, GAMMA-AL2O3 AND ACTIVE CHARCOAL AS CATALYSTS FOR THE OXIDATION OF 2-MERCAPTOETHANOL publication-title: MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS contributor: fullname: WOHRLE, D – volume: 19 start-page: 3231 year: 1989 ident: WOS:A1989AY32200017 article-title: REACTION OF 4-NITROPHTHALONITRILE WITH CARBONATE, NITRITE, AND FLUORIDE publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: WOHRLE, D – volume: 3 start-page: 129 year: 1991 ident: WOS:A1991FD14700002 article-title: ORGANIC SOLAR-CELLS publication-title: ADVANCED MATERIALS contributor: fullname: WOHRLE, D – volume: 42 start-page: 3548 year: 1909 ident: WOS:A1993KN23400003.19 publication-title: CHEM BER contributor: fullname: VILLINGER V – volume: 11 start-page: 447 year: 1981 ident: WOS:A1981LT36000005 article-title: A PREFERRED METHOD FOR IMIDE PREPARATION publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: CROCKETT, GC – volume: 18 start-page: 91 year: 1992 ident: WOS:A1992HM21000002 article-title: EFFICIENT SYNTHESIS OF PHTHALOCYANINES AND RELATED MACROCYCLIC-COMPOUNDS IN THE PRESENCE OF ORGANIC-BASES publication-title: DYES AND PIGMENTS contributor: fullname: WOHRLE, D |
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| Snippet | 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... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | A SIMPLE SYNTHESIS OF 4,5-DISUBSTITUTED 1,2-DICYANOBENZENES AND 2,3,9,10,16,17,23,24-OCTASUBSTITUTED PHTHALOCYANINES |
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