GB977478A - Tetracyano-benzoquinone-(1:4) and processes for its manufacture - Google Patents

Tetracyano-benzoquinone-(1:4) and processes for its manufacture

Info

Publication number
GB977478A
GB977478A GB5916/62A GB591662A GB977478A GB 977478 A GB977478 A GB 977478A GB 5916/62 A GB5916/62 A GB 5916/62A GB 591662 A GB591662 A GB 591662A GB 977478 A GB977478 A GB 977478A
Authority
GB
United Kingdom
Prior art keywords
compound
hydroquinone
complexes
dicyano
benzene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5916/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB977478A publication Critical patent/GB977478A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
    • C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises tetracyanobenzoquinone and hydroquinone, the former being obtained from the latter by reaction with nitrous gases. The hydroquinone is prepared by contacting a compound of formula (I) <FORM:0977478/C1/1> with an alkali or alkaline earth metal cyanide in a C1- 4 aliphatic alcohol; X is halogen, alkoxy or NR1R2 which is a ring containing 2-5 methylene groups wherein the polymethylene chain may be interrupted by oxygen, or in which R1 and R2 are H, C1- 4-alkyl or phenyl-C1- 3-alkyl. The compounds of the invention form complexes with aromatic compounds, in particular 1:1 complexes with pyrene; benzene, toluene, xylene, naphthalene and chrysene are also specified as complex-formers. The hydroquinone gives a dimethyl ether with CH2N2. Starting materials. The dialkoxydicyanoquinones are formed by action of an alcohol or the 3,6-dihalogen compound or of a diazoalkane or the 3,6-dihydroxy compound. The diaminodicyanoquinones are formed by action of ammonia or the appropriate amine on the 3,6-dihalogen compound or on the 3,6-dialkoxy compound, the latter method being used to prepare 2,5-dicyano-3, 6-dimorpholino, piperidino ethyleneimino and n-hexylamino-benzoquinones. The 2,5-dicyano-3, 6-dihydroxyquinone is formed by (a) hydrolysing (I) (e.g. X=Br, morpholine or O(Me) or (b) hydrolysing the reaction product of hydrogen halide and 2,5-dicyanoquinone. The latter compound is made by converting 2,5-dihydroxy diethyl terephthalate to the amide, alkylating the -OH groups, converting to dinitrile, dialkylating and oxidising with nitrous gases; it forms dicyanotetraacetoxy-benzene by reductive acetylation. The 2,5-dicyano-3, 6-diiodo and difluoro quinones are made, respectively, by reaction of the dibromoquinone with NaI/acetone and of the dichloroquinone with KF/dimethyl sulphoxide. The dicyanodibromoquinone is prepared thus: 2,5-dimethoxy-3, 6-dibromo-diethyl-terephthalate, which is obtained by action of Br2/AlCl3 on 2,5-dihydroxy-diethyl-terephthalate followed by Me2SO4 is hydrolysed and converted to the diamide via the acid chloride, and then to the dinitrile which is demethylated with AlCl3/NaCl giving the desired hydroquinone which is oxadised with nitrous gases.ALSO:1: 1 complexes of pyrene with tetracyano-benzoquinone and tetracyanohydroquinone are described; complexes of these tetracyano-compounds with benzene, toluene, xylene, naphthalene and chrysene may also be formed.
GB5916/62A 1961-02-15 1962-02-15 Tetracyano-benzoquinone-(1:4) and processes for its manufacture Expired GB977478A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF33208A DE1238894B (en) 1961-02-15 1961-02-15 Process for the preparation of tetracyano-benzoquinone- (1, 4)

Publications (1)

Publication Number Publication Date
GB977478A true GB977478A (en) 1964-12-09

Family

ID=7094994

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5916/62A Expired GB977478A (en) 1961-02-15 1962-02-15 Tetracyano-benzoquinone-(1:4) and processes for its manufacture

Country Status (6)

Country Link
JP (3) JPS3924797B1 (en)
BE (1) BE613979A (en)
CH (1) CH428699A (en)
DE (1) DE1238894B (en)
GB (1) GB977478A (en)
NL (1) NL274730A (en)

Also Published As

Publication number Publication date
NL274730A (en)
BE613979A (en) 1962-08-16
JPS402661B1 (en) 1965-02-11
JPS3924797B1 (en) 1964-11-05
JPS402660B1 (en) 1966-02-11
CH428699A (en) 1967-01-31
DE1238894B (en) 1967-04-20

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